2-mercaptobenzothiazole and its derivatives: Syntheses, reactions and applications

Current Organic Chemistry

Volumn 16, Issue 13, 2012, Pages 1555-1580

  Wu, Feng Ling ^a   Hussein, Waleed M ^a,b   Ross, Benjamin P ^a   McGeary, Ross P ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b Helwan   (Egypt)

Author keywords

2 mercaptobenzothiazole; Enantioselective additions; Epoxide deoxygenation; Julia olefination; Tautomerism; Vulcanisation

Indexed keywords

REDOX REACTIONS; SUBSTITUTION REACTIONS; VULCANIZATION;

2-MERCAPTOBENZOTHIAZOLE; DEOXYGENATIONS; DERIVATIVE SYNTHESIS; ENANTIOSELECTIVE ADDITION; EPOXIDE DEOXYGENATION; JULIA OLEFINATION; OLEFINATION REACTION; SYNTHESIS REACTION; TAUTOMERISM; VULCANISATION;

RUBBER;

EID: 84862566296     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212800840964     Document Type: Review

References (257)

1. Hofmann, A. W. Orthamidophenyl mercaptan. Chem. Ber. 1887, 20, 1788-1797.
2. Stierle, A. A.; Cardellina Ii, J. H.; Singleton, F. L. Benzothiazoles from a putatitve bacterial symbiont of the marine sponge Tedania ignis. Tetrahedron Lett. 1991, 32, 4847-4848.
3. Chipinda, I.; Hettick, J. M.; Simoyi, R. H.; Siegel, P. D. Oxidation of 2- Mercaptobenzothiazole in Latex Gloves and Its Possible Haptenation Pathway. Chem. Res. Toxicol. 2007, 20, 1084-1092.
4. Harizi, A.; Romdhane, A.; Mighri, Z. Synthesis and reactivity of benzoxa(thia)zol-2-thiones: new route to 2-alkylthiobenzoxa(thia)zoles. Tetrahedron Lett. 2000, 41, 5833-5835.
5. Singh, M. S.; Singh, P.; Singh, S. Synthesis of benzoxazol-2-ones, benzothiazol-2-ones and their 2-thione analogs: efficient conversion of 2- thione to 2-oxo analogs. Indian J. Chem., Sect B 2007, 46B, 1666-1671.
6. Ballabeni, M.; Ballini, R.; Bigi, F.; Maggi, R.; Parrini, M.; Predieri, G.; Sartori, G. Synthesis of Symmetrical N,N'-Disubstituted Thioureas and Heterocyclic Thiones from Amines and CS2 over a ZnO/Al2O3 Composite as Heterogeneous and Reusable Catalyst. J. Org. Chem. 1999, 64, 1029-1032.
7. Sugimoto, H.; Makino, I.; Hirai, K. Activation of dithiocarbamate by 2- halothiazolium salts. J. Org. Chem. 1988, 53, 2263-2267.
8. Neyts, J.; Das, A. R.; Hung, S. C.; Hwu, J. R.; Singha, R. Preparation of benzimidazole-containing nucleosides as antiviral agents. WO Patent 128086, 2007.
9. Kretzschmar, E.; Laban, G. Process for preparation of 2- mercaptobenzimidazoles, -oxazoles and -thiazoles. DE Patent 4230923A1, 1993.
10. Seidel, P. Derivatives of carbonylorthamidophenol and of thiocarborthamidophenol. J. Prakt. Chem. 1890, 42, 445-457.
11. Tanaka, A.; Fukuoka, M.; Adachi, T.; Yamaha, T. Syntheses of carbon-14- and sulfur-35-labeled 2-(morpholinothio)benzothiazoles and carbon-14- labeled 2-(cyclohexylaminothio)benzothiazoles. J. Labelled Compd. Radiopharm. 1986, 23, 405-413.
12. Teppema, J.; Sebrell, L. B. Researches on Mercaptothiazoles. I. J. Am. Chem. Soc. 1927, 49, 1748-1758.
13. Dunbrook, R. F.; Zimmermann, M. H. A Method for the Preparation of 2- Mercaptobenzothiazole. J. Am. Chem. Soc. 1934, 56, 2734-2736.
14. Zhang, L.; Fan, J.; Vu, K.; Hong, K.; Le, B. J.-Y.; Shi, J.; Biamonte, M.; Busch, D. J.; Lough, R. E.; Grecko, R.; Ran, Y.; Sensintaffar, J. L.; Kamal, A.; Lundgren, K.; Burrows, F. J.; Mansfield, R.; Timony, G. A.; Ulm, E. H.; Kasibhatla, S. R.; Boehm, M. F. 7'-Substituted Benzothiazolothio- and Pyridinothiazolothio-Purines as Potent Heat Shock Protein 90 Inhibitors. J. Med. Chem. 2006, 49, 5352-5362.
15. Tzanova, T.; Gerova, M.; Petrov, O.; Karaivanova, M.; Bagrel, D. Synthesis and antioxidant potential of novel synthetic benzophenone analogues. Eur. J. Med. Chem. 2009, 44, 2724-2730.
16. Yang, G.; Zhao, P.; Huang, W.; Liu, Z. Methoxy acrylate fungicide, its preparation process and application for prevention and control of plant fungal diseases. CN Patent 101268780A, 2008.
17. Chaudhuri, N. C. Convenient strategies for the preparation of modified 2(3H)-benzothiazolethiones. Synth. Commun. 1996, 26, 3783-3790.
18. Logemann, W.; Galimberti, S.; Tosolini, G.; Carneri, I. D.; Coppi, G. Antitubercular action in vivo and in vitro of some benzothiazole derivatives. Farmaco, Ed. Sci. 1961, 16, 795-816.
19. Jiang, L.-L.; Zuo, Y.; Wang, Z.-F.; Tan, Y.; Wu, Q.-Y.; Xi, Z.; Yang, G.-F. Design and Syntheses of Novel N-(Benzothiazol-5-yl)-4,5,6,7-tetrahydro- 1H-isoindole-1,3(2H)-dione and N-(Benzothiazol-5-yl)isoindoline-1,3-dione as Potent Protoporphyrinogen Oxidase Inhibitors. J. Agric. Food Chem. 2011, 59, 6172-6179.
20. Chen, J.-L. Preparation of N-substituted benzenesulfonamide as PPARg modulators for use in the treatment of neoplasm, osteoporosis, inflammation and related diseases. WO Patent 086904A2, 2005.
21. Gatard, S.; Blanchard, S.; Schollhorn, B.; Gouzerh, P.; Proust, A.; Boubekeur, K. Electroactive Benzothiazole Hydrazones and Their [Mo6O19]2- Derivatives: Promising Building Blocks for Conducting Molecular Materials. Chem. Eur. J. 2010, 16, 8390-8399.
22. Jiang, L.-L.; Tan, Y.; Zhu, X.-L.; Wang, Z.-F.; Zuo, Y.; Chen, Q.; Xi, Z.; Yang, G.-F. Design, Synthesis, and 3D-QSAR Analysis of Novel 1,3,4- Oxadiazol-2(3H)-ones as Protoporphyrinogen Oxidase Inhibitors. J. Agric. Food Chem. 2010, 58, 2643-2651.
23. Martin, R.; Flatt, B. T.; Wang, T.-L.; Kahl, J. D. Preparation of phenylimino thiazolylidene thiazolidinones and other heterocyclic modulators of nuclear receptors with therapeutic uses. WO Patent 060078A2, 2003.
24. Ma, Y.; Wang, Y.; Zhou, Z. Synthesis of 2-chloro-4- (chloromethyl)benzothiazole. Jingxi Huagong Zhongjianti 2009, 39, 7-8.
25. Singh, B.; Pennock, P. O.; Lesher, G. Y.; Bacon, E. R.; Page, D. F. An efficient and novel synthesis of fused thiazol-2(3H)-ones. Heterocycles 1993, 36, 133-144.
26. Franchini, C.; Muraglia, M.; Corbo, F.; Florio, M. A.; Di, M. A.; Rosato, A.; Matucci, R.; Nesi, M.; van, B. F.; Vitali, C. Synthesis and Biological Evaluation of 2-Mercapto-1,3-benzothiazole Derivatives with Potential Antimicrobial Activity. Arch. Pharm. 2009, 342, 605-613.
27. Karlsson, H. J.; Bergqvist, M. H.; Lincoln, P.; Westman, G. Syntheses and DNA-binding studies of a series of unsymmetrical cyanine dyes: structural influence on the degree of minor groove binding to natural DNA. Bioorg. Med. Chem. 2004, 12, 2369-2384.
28. Zhu, L.; Zhang, M. Ortho-Selective Nucleophilic Aromatic Substitution Reactions of Polyhaloanilines with Potassium/Sodium O-Ethyl Xanthate: A Convenient Access to Halogenated 2(3H)-Benzothiazolethiones. J. Org. Chem. 2004, 69, 7371-7374.
29. Zhu, L.; Zhang, M.; Dai, M. A convenient synthesis of 2-mercapto and 2- chlorobenzothiazoles. J. Heterocycl. Chem. 2005, 42, 727-730.
30. Wu, W.-L.; Burnett, D. A.; Spring, R.; Greenlee, W. J.; Smith, M.; Favreau, L.; Fawzi, A.; Zhang, H.; Lachowicz, J. E. Dopamine D1/D5 Receptor Antagonists with Improved Pharmacokinetics: Design, Synthesis, and Biological Evaluation of Phenol Bioisosteric Analogues of Benzazepine D1/D5 Antagonists. J. Med. Chem. 2005, 48, 680-693.
31. Fritch, P. C.; McNaughton-Smith, G.; Amato, G. S.; Burns, J. F.; Eargle, C. W.; Roeloffs, R.; Harrison, W.; Jones, L.; Wickenden, A. D. Novel KCNQ2/Q3 Agonists as Potential Therapeutics for Epilepsy and Neuropathic Pain. J. Med. Chem. 2010, 53, 887-896.
32. Huang, W.; Tan, Y.; Ding, M.-W.; Yang, G.-F. Improved synthesis of 2- (3H)benzothiazolethiones under microwave irradiation. Synth. Commun. 2007, 37, 369-376.
33. Huang, W.; Yang, G.-F. Microwave-assisted, one-pot syntheses and fungicidal activity of polyfluorinated 2-benzylthiobenzothiazoles. Biorg. Med. Chem. 2006, 14, 8280-8285.
34. Easmon, J.; Heinisch, G.; Hofmann, J.; Langer, T.; Grunicke, H. H.; Fink, J.; Purstinger, G. Thiazolyl and benzothiazolyl hydrazones derived from a-(N)- acetylpyridines and diazines: synthesis, antiproliferative activity and CoMFA studies. Eur. J. Med. Chem. 1997, 32, 397-408.
35. Leymarie-Beljean, M.; Pays, M.; Richer, J. C. Heterocyclic hydrazines and hydrazones. III. Synthesis of naphtho[2,3-d]thiazole derivatives. J. Heterocycl. Chem. 1980, 17, 1175-1179.
36. Silva, G. L.; Ediz, V.; Yaron, D.; Armitage, B. A. Experimental and computational investigation of unsymmetrical cyanine dyes: Understanding torsionally responsive fluorogenic dyes. J. Am. Chem. Soc. 2007, 129, 5710-5718.
37. Wang, F.; Cai, S.; Wang, Z.; Xi, C. Synthesis of 2-Mercaptobenzothiazoles via DBU-Promoted Tandem Reaction of o-Haloanilines and Carbon Disulfide. Org. Lett. 2011, 13, 3202-3205.
38. Sebrell, L. B.; Boord, C. E. The preparation and properties of 1- mercaptobenzothiazole, its homologs and derivatives. J. Am. Chem. Soc. 1923, 45, 2390-2399.
39. Cobb, A.; Peemans, R.; Coenegrachts, P.; Isaacs, N. S.; Hilton, M. J.; Coulson, M. Acid catalyzed process for preparing 2-mercaptobenzothiazole. WO Patent 9746544A1, 1997.
40. Krizanovic, K.; Muntagova, L. Crystalization method for obtaining pure 2- mercaptobenzothiazole from its cyclocondensation synthesis reaction mixture containing aniline, carbon disulfide and sulfur. WO Patent 2005061471A1, 2005.
41. Kelly, W. J. Mercaptobenzothiazole. US Patent 1631871, 1927.
42. Galliford, C. V.; Voronin, K.; Hesk, D.; Koharski, D.; McNamara, P. Rapid synthesis of a 13C6-benzothiazolium salt from 13C6-aniline. J. Labelled Compd. Radiopharm. 2011, 54, 229-232.
43. Murti, Y.; Pathak, D. Synthesis and antimicrobial screening of substituted 2- mercaptobenzothiazoles. J. Pharm. Res. 2008, 7, 153-155.
44. Isaacs, N. S.; Ismail, Y.; Hilton, M. J.; Coulson, M. Mechanism of formation of benzothiazole-2-thiol. J. Phys. Org. Chem. 1998, 11, 1-9.
45. Scott, W.; Watt, G. W. Reactions in the Thiazole Series. I. Reactions of 2- Chlorobenzothiazoles with Thioureas. J. Org. Chem. 1937, 2, 148-156.
46. Cressier, D.; Prouillac, C.; Hernandez, P.; Amourette, C.; Diserbo, M.; Lion, C.; Rima, G. Synthesis, antioxidant properties and radioprotective effects of new benzothiazoles and thiadiazoles. Bioorg. Med. Chem. 2009, 17, 5275-5284.
47. Foye, W. O.; Abood, N.; Kauffman, J. M.; Kim, Y.-H.; Patel, B. R. A direct synthesis of heterocyclic thiols. Phosphorus Sulfur 1980, 8, 205-207.
48. Jacobson, P.; Frankenbacher, A. Formation of thianhydro-compounds. Chem. Ber. 1891, 24, 1400-1411.
49. Rassow, B.; Dohle, W.; Reim, E. New derivatives of benzothiazole and its homologs. J. Prakt. Chem. 1916, 93, 183-253.
50. Lecher, H. Z.; Hardy, E. M. Some New Methods for Preparing Bunte Salts. J. Org. Chem. 1955, 20, 475-487.
51. Singh, G. P.; Godbole, H. M.; Nehate, S. P.; Mahajan, P. R. 2'- Benzothiazolylthioesters of N-Substituted Alpha Amino Acids: Versatile Intermediates for Synthesis of ACE Inhibitors. Synth. Commun. 2005, 35, 243-248.
52. Chary, K. P.; Rajaram, S.; Iyengar, D. S. A Rapid and Efficient Cleavage of Organic Disulfides to Mercaptans Using ZrCl4/NaBH4. Synth. Commun. 2000, 30, 3905-3911.
53. Zhang, J.; Gao, X.; Zhang, C.; Zhang, C.; Luan, J.; Zhao, D. Mild and Efficient Deoxygenation of Sulfoxides to Sulfides Using HfCl4/KBH4 System. Synth. Commun. 2010, 40, 1794-1801.
54. Sato, R.; Akaishi, R.; Goto, T.; Saito, M. New Birch type reduction. Halogen or halides-activated reduction of disulfides to thiols with aluminum in liquid ammonia. Bull. Chem. Soc. Jpn. 1987, 60, 773-774.
55. Boraei, A. A. A.; Ahmed, I. T.; Hamed, M. M. A. Acid Dissociation Constants of Some Mercaptobenzazoles in Aqueous-Organic Solvent Mixtures. J. Chem. Eng. Data 1996, 41, 787-790.
56. Roux, M. V.; Temprado, M.; Jimenez, P.; Foces-Foces, C.; Notario, R.; Parameswar, A. R.; Demchenko, A. V.; Chickos, J. S.; Deakyne, C. A.; Liebman, J. F. Experimental and Theoretical Study of the Structures and Enthalpies of Formation of 3H-1,3-Benzoxazole-2-thione, 3H-1,3- Benzothiazole-2-thione, and Their Tautomers. J. Phys. Chem. A 2010, 114, 6336-6341.
57. Rai, A. K.; Singh, R.; Singh, K. N.; Singh, V. B. FTIR, Raman spectra and ab initio calculations of 2-mercaptobenzothiazole. Spectrochim. Acta, Part A 2006, 63A, 483-490.
58. Böhlig, H.; Ackermann, M.; Billes, F.; Kudra, M. Vibrational analysis of benzothiazoline-2-thione. Spectrochim. Acta, Part A 1999, 55, 2635-2646.
59. Mohan, S.; Prabakaran, A. R.; Prameela, S. FTIR and Raman spectra of benzothiazole and benzothiazolethiol. Indian J. Pure Appl. Phys. 1991, 29, 672-677.
60. Mohamed, T. A.; Mustafa, A. M.; Zoghaib, W. M.; Afifi, M. S.; Farag, R. S.; Badr, Y. Reinvestigation of benzothiazoline-2-thione and 2- mercaptobenzothiazole tautomers: Conformational stability, barriers to internal rotation and DFT calculations. J. Mol. Struct. 2008, 868, 27-36.
61. Contini, G.; Di, C. V.; Stranges, S.; Richter, R.; Alagia, M. Gas-Phase Photoemission Study of 2-Mercaptobenzothiazole. J. Phys. Chem. A 2002, 106, 2833-2837.
62. Chesick, J. P.; Donohue, J. The molecular and crystal structure of 2- mercaptobenzothiazole. Acta Crystallogr., Sect. B: Struct. Sci. 1971, 27, 1441-1444.
63. Flett, M. S. C. The infrared spectra of some thio amides. J. Chem. Soc. 1953, 347-348.
64. Bellamy, L. J.; Rogasch, P. E. Proton transfer in hydrogen-bonded systems. Proc. R. Soc. London, Ser. A 1960, 257, 98-108.
65. Griffiths, P. J. F.; Morgan, G. D.; Ellis, B. Infrared spectra and hydrogen bonding of heterocyclic thioamides. Spectrochim. Acta, Part A 1972, 28, 1899-1907.
66. Koch, H. P. 92. Absorption spectra and structure of organic sulphur compounds. Part III. Vulcanisation accelerators and related compounds. J. Chem. Soc. 1949, 401-408.
67. Morton, R. A.; Stubbs, A. L. 281. Absorption spectra of some sulphur compounds. J. Chem. Soc. 1939, 1321-1324.
68. Sebrell, L. B.; Boord, C. E. Mercaptobenzothiazole and its derivatives as accelerators of rubber vulcanization. J. Ind. Eng. Chem. 1923, 15, 1009-1014.
69. Hofmann, W. Rubber Technology Handbook; Hanser Publishers: Munich; New York, 1988.
70. Heideman, G.; Datta, R. N.; Noordermeer, J. W. M.; van, B. B. Activators in accelerated sulfur vulcanization. Rubber Chem. Technol. 2004, 77, 512-541.
71. Engels, H.-W.; Weidenhaupt, H.-J.; Pieroth, M.; Hofmann, W.; Menting, K.- H.; Mergenhagen, T.; Schmoll, R.; Uhrlandt, S. In Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA, 2011.
72. Morrison, N. J.; Porter, M. Temperature effects on the stability of intermediates and crosslinks in sulfur vulcanization. Rubber Chem. Technol. 1984, 57, 63-85.
73. Aprem, A. S.; Joseph, K.; Thomas, S. Recent developments in crosslinking of elastomers. Rubber Chem. Technol. 2005, 78, 458-488.
74. Van Der Horst, M.; Hendrikse, K. G.; Woolard, C. D. The role of thiol intermediates in 2-mercaptobenzothiazole accelerated sulfur vulcanization of rubber model compounds. J. Appl. Polym. Sci. 2003, 89, 47-54.
75. Ohsawa, M.; Suëtaka, W. Spectro-electrochemical studies of the corrosion inhibition of copper by mercaptobenzothiazole. Corros. Sci. 1979, 19, 709-722.
76. Musiani, M. M.; Mengoli, G.; Fleischmann, M.; Lowry, R. B. An electrochemical and SERS investigation of the influence of pH on the effectiveness of some corrosion inhibitors of copper. J. Electroanal. Chem. 1987, 217, 187-202.
77. Trabanelli, G.; Carassitti, V. In Advances in corrosion science and technology; Fontana, M. G.; Staehle, R. W., Eds.; Plenum Press: New York; London, 1970, p 147.
78. Thibault, S.; Talbot, J. Use of infrared spectrometry in studying corrosion phenomena. Application to the determination of compounds adsorbed on copper surfaces. Bull. Soc. Chim. Fr. 1972, 4, 1348-1354.
79. Thibault, S.; Talbot, J. Application of multiple reflection infrared spectrometry to the study of several corrosion problems. Metaux: Corrosion- Industrie 1975, 50, 51-55.
80. Satake, M.; Ishida, K.; Puri, B. K.; Usami, S. Preconcentration of copper in water samples with mercaptobenzothiazole on naphthalene. Anal. Chem. 1986, 58, 2502-2504.
81. Bera, B. C.; Chakrabartty, M. M. Spectrophotometric determination of selenium with 2-mercaptobenzothiazole. Analyst 1968, 93, 50-55.
82. Bera, B. C.; Chakrabartty, M. M. Spectrophotometric determination of osmium with 2-mercaptobenzothiazole. Microchem. J. 1966, 11, 420-429.
83. Majumdar, A. K.; Chakrabartty, M. M. Spectrophotometric determination of palladium: A comparative study of 2-mercaptobenzothiazole and 2- mercaptobenzimidazole as analytical reagents. Anal. Chim. Acta 1959, 20, 379-385.
84. Yoon, J.-I.; Choi, H.-S. Determination of Cd (II) after preconcentration onto microcrystalline p-dichlorobenzene loaded with 2-mercaptobenzothiazole. J. Korean Chem. Soc. 2009, 53, 27-33.
85. Saluja, P.; Kaur, N.; Singh, N.; Jang, D. O. A benzthiazole-based tripodal chemosensor for Ba2+ recognition under biological conditions. Tetrahedron Lett. 2011, 52, 6705-6708.
86. Nawrocki, S. T.; Drake, K. D.; Watson, C. F.; Foster, G. D.; Maier, K. J. Comparative Aquatic Toxicity Evaluation of 2- (Thiocyanomethylthio)benzothiazole and Selected Degradation Products Using Ceriodaphnia dubia. Arch. Environ. Contam. Toxicol. 2005, 48, 344-350.
87. Reemtsma, T.; Fiehn, O.; Kalnowski, G.; Jekel, M. Microbial Transformations and Biological Effects of Fungicide-Derived Benzothiazoles Determined in Industrial Wastewater. Environ. Sci. Technol. 1995, 29, 478-485.
88. Corban, G. J.; Hadjikakou, S. K.; Tsipis, A. C.; Kubicki, M.; Bakas, T.; Hadjiliadis, N. Inhibition of peroxidase-catalyzed iodination by thioamides: experimental and theoretical study of the antithyroid activity of thioamides. New J. Chem. 2011, 35, 213-224.
89. Rohrig, U. F.; Awad, L.; Grosdidier, A.; Larrieu, P.; Stroobant, V.; Colau, D.; Cerundolo, V.; Simpson, A. J. G.; Vogel, P.; Van, d. E. B. J.; Zoete, V.; Michielin, O. Rational Design of Indoleamine 2,3-Dioxygenase Inhibitors. J. Med. Chem. 2010, 53, 1172-1189.
90. Supuran, C. T.; Saramet, I.; Bangiu, M. D. Carbonic anhydrase inhibitors. 31. Isoenzyme Ii inhibition with mercaptoazoles. Rev. Roum. Chim. 1995, 40, 1227-1232.
91. Kocí, J.; Klimesová, V.; Waisser, K.; Kaustová, J.; Dahse, H.-M.; Möllmann, U. Heterocyclic benzazole derivatives with antimycobacterial In vitro activity. Bioorg. Med. Chem. Lett. 2002, 12, 3275-3278.
92. Toropov, A. A.; Toropova, A. P.; Benfenati, E. SMILES-based optimal descriptors: QSAR modeling of carcinogenicity by balance of correlations with ideal slopes. Eur. J. Med. Chem. 2010, 45, 3581-3587.
93. Johnson, F. M. Carcinogenic chemical-response fingerprint for male F344 rats exposed to a series of 195 chemicals: implications for predicting carcinogens with transgenic models. Environ. Mol. Mutagen. 1999, 34, 234-245.
94. Sorahan, T. Cancer risks in chemical production workers exposed to 2- mercaptobenzothiazole. Occup. Environ. Med. 2009, 66, 269-273.
95. Chipinda, I.; Zhang, X.-D.; Simoyi, R. H.; Siegel, P. D. Mercaptobenzothiazole allergenicity-role of the thiol group. Cutan. Ocul. Toxicol. 2008, 27, 103-116.
96. Ramadas, K.; Janarthanan, N. Convenient Synthesis of Chloromethyl Thioaromatics. Synth. Commun. 1999, 29, 1003-1007.
97. Baehring-Kuhlmey, S. R. Ethoxzolamide. Drugs Today 1978, 14, 205-209.
98. Thiry, A.; Supuran, C. T.; Masereel, B.; Dogne, J.-M. Recent Developments of Carbonic Anhydrase Inhibitors as Potential Anticancer Drugs. J. Med. Chem. 2008, 51, 3051-3056.
99. Naya, A.; Kobayashi, K.; Ishikawa, M.; Ohwaki, K.; Saeki, T.; Noguchi, K.; Ohtake, N. Structure-Activity Relationships of 2- (Benzothiazolylthio)acetamide Class of CCR3 Selective Antagonist. Chem. Pharm. Bull. 2003, 51, 697-701.
100. Dumas, J.; Brittelli, D.; Chen, J.; Dixon, B.; Hatoum-Mokdad, H.; König, G.; Sibley, R.; Witowsky, J.; Wong, S. Synthesis and structure activity relationships of novel small molecule cathepsin D inhibitors. Bioorg. Med. Chem. Lett. 1999, 9, 2531-2536.
101. Pathak, U.; Pandey, L. K.; Mathur, S. Efficient and Convenient Oxidation of Thiols to Symmetrical Disulfide with Silica-PCl5/NaNO2 in Water. Synth. Commun. 2009, 39, 2923-2927.
102. Vangala, V. R.; Bhogala, B. R.; Dey, A.; Desiraju, G. R.; Broder, C. K.; Smith, P. S.; Mondal, R.; Howard, J. A. K.; Wilson, C. C. Correspondence between Molecular Functionality and Crystal Structures. Supramolecular Chemistry of a Family of Homologated Aminophenols. J. Am. Chem. Soc. 2003, 125, 14495-14509.
103. Joshaghani, M.; Khosropour, A. R.; Jafary, H.; Mohammadpoor-Baltork, I. Mild and highly efficient preparation of symmetrical disulfides and diselenides using bipyridinium hydrobromide perbromide as a new oxidative reagent. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 117-123.
104. Misra, A. K.; Agnihotri, G. Nitric acid-mediated oxidative transformation of thiols to disulfides. Synth. Commun. 2004, 34, 1079-1085.
105. Tajbakhsh, M.; Hosseinzadeh, R.; Shakoori, A. 2,6-Dicarboxypyridinium chlorochromate. An efficient and selective reagent for the oxidation of thiols to disulfides and sulfides to sulfoxides. Tetrahedron Lett. 2004, 45, 1889-1893.
106. Mohammadpoor-Baltork, I.; Memarian, H.; Bahrami, K. Selective and convenient oxidation of thiols to disulfides using nbutyltriphenylphosphonium dichromate (Bun PPh3)2Cr2O7 in solution, under solvent-free conditions, and microwave irradiation. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 2315-2321.
107. Hosseinzadeh, R.; Tajbakhsh, M.; Khaledi, H.; Ghodrati, K. Ethylenebis(Nmethylimidazolium) chlorochromate (EBMICC). An efficient and selective reagent for the oxidation of thiols to disulfides. Monatsh. Chem. 2007, 138, 871-873.
108. Karimi, B.; Zareyee, D. Hexamethyldisilazane (HMDS) promotes highly efficient oxidative coupling of thiols by DMSO under nearly neutral reaction conditions. Synlett 2002, 346-348.
109. Iranpoor, N.; Zeynizadeh, B. Air oxidative coupling of thiols to disulfides catalyzed by Fe(III)/NaI. Synthesis 1999, 49-50.
110. Shah, S. T. A.; Khan, K. M.; Fecker, M.; Voelter, W. A novel method for the syntheses of symmetrical disulfides using CsF-Celite as a solid base. Tetrahedron Lett. 2003, 44, 6789-6791.
111. Bagiyan, G. A.; Koroleva, I. K.; Soroka, N. V.; Ufimtsev, A. V. Complexes of Copper(I) with Dimercapto Compounds as Catalysts for Oxidation of Mercaptans and Hydrogen Sulfide with Molecular Oxygen in Aqueous Solutions. Russ. J. Appl. Chem. 2003, 76, 88-94.
112. Parkanyi, C.; Abdelhamid, A. O. Photodegradation of pesticides: photolysis of 2-mercaptobenzothiazole and 2-mercaptobenzimidazole. Heterocycles 1985, 23, 2917-2926.
113. Firouzabadi, H.; Naderi, M.; Sardarian, A.; Vessal, B. The facile oxidation of thiols to disulfides with bis(2,2'-bipyridyl)copper(II) permanganate. Synth. Commun. 1983, 13, 611-615.
114. Firouzabadi, H.; Iranpoor, N.; Hajipoor, G.; Toofan, J. Tris[trinitratocerium(IV)] paraperiodate [(NO3)3Ce]3H2IO6, an efficient and a versatile oxidant in organic synthesis. Synth. Commun. 1984, 14, 1033-1042.
115. Frachey, G.; Crestini, C.; Bernini, R.; Saladino, R.; Mincione, E. Oxidation of 2-mercaptobenzo heterazoles by dimethyldioxirane. A new method for a synthesis of C-2 substituted benzimidazole, benzoxazole, and benzothiazole derivatives. Heterocycles 1994, 38, 2621-2630.
116. Fishwick, B. R.; Rowles, D. K.; Stirling, C. J. M. Bromonitromethane: a versatile electrophile. J. Chem. Soc., Perkin Trans. 1 1986, 1171-1179.
117. Vandavasi, J. K.; Hu, W.-P.; Chen, C.-Y.; Wang, J.-J. Efficient synthesis of unsymmetrical disulfides. Tetrahedron 2011, 67, 8895-8901.
118. Hronec, M.; Stolcova, M.; Liptay, T. Selective oxidation of 2- mercaptobenzothiazole. Stud. Surf. Sci. Catal. 1994, 82, 667-673.
119. Kouge, K.; Koizumi, T.; Ishibashi, N.; Okai, H. New taste-blind substances. Studies on the sensory divergence of bitterness to the taste-blindness of 2- mercaptoimidazoline, 2-mercaptobenzothiazole and their derivatives, with special reference to their molecular structure. Agric. Biol. Chem. 1987, 51, 1941-1945.
120. Wu, F.-L.; Ross, B. P.; McGeary, R. P. New Methodology for the Conversion of Epoxides to Alkenes. Eur. J. Org. Chem. 2010, 1989-1998.
121. Grivas, S.; Ronne, E. Facile desulfurization of cyclic thioureas by hydrogen peroxide in acetic acid. Acta Chem. Scand. 1995, 49, 225-229.
122. Kucera, Z.; Karlik, M.; Krofta, J. Iodometric determination of 2- mercaptobenzthiazole by coulometric titration. Collect. Czech. Chem. Commun. 1982, 47, 588-593.
123. Brownbridge, P.; Jowett, I. C. One-pot synthesis of sulfinic esters from disulfides. Synthesis 1988, 252-254.
124. Weibull, B. Reduction of 2-mercaptobenzothiazole to benzothiazole. Acta Chem. Scand. 1962, 16, 1052.
125. Blomquist, A. T.; Diuguid, L. I. Benzothiazoles. II. Nuclear chlorination in the Herz process. J. Org. Chem. 1947, 12, 718-725.
126. Badger, G. M.; Kowanko, N.; Sasse, W. H. F. Synthetic applications of activated metal catalysts. VI. Desulfurizations with Raney cobalt. J. Chem. Soc. 1959, 440-444.
127. Badger, G. M.; Kowanko, N. Synthetic applications of activated metal catalysts. III. Desulfurization of thiazoles with Raney nickel. J. Chem. Soc. 1957, 1652-1657.
128. Lazier, W. A.; Signaigo, F. K. Thiols. US Patent 2402642, 1946.
129. Hauptmann, H.; Walter, W. F. The Action of Raney Nickel on Organic Sulfur Compounds. Chem. Rev. 1962, 62, 347-404.
130. Hagedorn, F.; Fiege, H.; Traenckner, H. J. Desulfurization of organic mercaptans and disulfides. DE Patent 4319574, 1994.
131. Teppema, J.; Sebrell, L. B. Researches on Thiazoles. II. The Nitration and Reduction of 2-Mercaptobenzothiazole and its Substuituted Derivatives. J. Am. Chem. Soc. 1927, 49, 1779-1785.
132. Mackie, A.; Misra, A. L. Preparation of thiazoles and benzothiazoles as possible anthelmintics. J. Chem. Soc. 1954, 4430-4432.
133. Hasan, C.; Hunter, R. F.; Firdaus, A. A. Unsaturation and tautomeric mobility of heterocyclic compounds. IX. The methylation of 5-substituted 1- thiolbenzothiazoles and the ultraviolet absorption of mobile and static derivatives of 1-thiolbenzothiazole. J. Chem. Soc. 1936, 1672-1675.
134. Suzuki, N.; Tanaka, Y.; Dohmori, R. Synthesis of antimicrobial agents. I. Synthesis and antimicrobial activities of thiazoloquinoline derivatives. Chem. Pharm. Bull. 1979, 27, 1-11.
135. Clark, R. B.; Elbaum, D. Preparation of novel piperazines as agonists of the α7 nAChR. WO Patent 146066A2, 2007.
136. Sharpe, C. J.; Palmer, P. J.; Evans, D. E.; Brown, G. R.; King, G.; Shadbolt, R. S.; Trigg, R. B.; Ward, R. J.; Ashford, A.; Ross, J. W. Basic ethers of 2- anilinobenzothiazoles and 2-anilinobenzoxazoles as potential antidepressants. J. Med. Chem. 1972, 15, 523-529.
137. Cagnoli, N.; Santamaria, L.; Ricci, A. Derivatives of benzothiazole. IV. Derivatives of 2-benzothiazolethioglycolic and 2-benzothiazolethiolactic acids. Ricerca Sci. 1958, 28, 2522-2525.
138. Kuznetsova, E. A.; Zhuravlev, S. V.; Stepanova, T. N. Synthesis in the 2- mercaptobenzothiazole series V. Thiazolidino[2, 3-b]-benzothiazolines. Chem. Heterocycl. Compd. 1967, 3, 197-200.
139. Davies, W. H.; Sexton, W. A. Reactions of benzothiazole derivatives. III. The interaction of 1-thiolbenzothiazoles and alcohols. J. Chem. Soc. 1942, 304-307.
140. Abramova, N. D.; Afonin, A. V.; Naumova, G. G. Benzothiazole-2-thione and benzothiazol-2-one in reaction with acetylene. Khim. Geterotsikl. Soedin. 1991, 270-271.
141. Stolcova, M.; Hronec, M. Catalyzed oxidation of 2-mercaptobenzothiazole to 2-hydroxybenzothiazole. Recl. Trav. Chim. Pays-Bas 1996, 115, 222-225.
142. Herdieckerhoff, E.; Tschunkur, E. Heterocyclic hydroxy compounds. US Patent 2108712, 1938.
143. Kandeel, M. M. Synthetic studies on some new diaryl sulphides and diaryl sulphones with fused heterocyclic rings. Bull. Pol. Acad. Sci., Chem. 2002, 50, 309-322.
144. Brown, R. N.; Cameron, R.; Chalmers, D. K.; Hamilton, S.; Luttick, A.; Krippner, G. Y.; McConnell, D. B.; Nearn, R.; Stanislawski, P. C.; Tucker, S. P.; Watson, K. G. 2-Ethoxybenzoxazole as a bioisosteric replacement of an ethyl benzoate group in a human rhinovirus (HRV) capsid binder. Bioorg. Med. Chem. Lett. 2005, 15, 2051-2055.
145. Giesbrecht, H. E.; Knight, B. J.; Tanguileg, N. R.; Emerson, C. R.; Blakemore, P. R. Thieme chemistry journal awardees - where are they now? Stereoselective synthesis of Z-configured a{belowdot}b-unsaturated macrocyclic lactones and diolides by intramolecular Julia-Kocienski olefination. Synlett 2010, 374-378.
146. Hoggarth, E. Preparation and reactivity of some 2- methanesulfonylbenzazoles. J. Chem. Soc. 1949, 3311-3315.
147. Suzuki, N.; Kadoya, S.; Dohmori, R. Synthetic chemotherapeutic agents. IV. Synthesis of 3-substituted thiazolo[5,4-f]quinoline derivatives. (2). Chem. Pharm. Bull. 1976, 24, 1050-1058.
148. Kadoya, S.; Suzuki, N.; Takamura, I.; Dohmori, R. Synthetic chemotherapeutic agents. III. Synthesis of 3-substituted thiazolo[5,4- f]quinoline derivatives. (1). Chem. Pharm. Bull. 1976, 24, 147-155.
149. Gueyrard, D.; Lorin, C.; Moravcova, J.; Rollin, P. A new intramolecular migration in thio sugar chemistry: S → O transfer of a benzothiazol-2-yl group in saccharidic sulfones. J. Carbohydr. Chem. 1999, 18, 317-331.
150. Sexton, W. A. Reactions of benzothiazole derivatives. I. The reactivity of the methylthiol group in quaternary salts of 1-methylthiobenzothiazole. J. Chem. Soc. 1939, 470-473.
151. Riemschneider, R.; Georgi, S. Benzothiazole derivatives. IV. Benzothiazole salts. Monatsh. Chem. 1960, 91, 623-629.
152. Ubaldini, I.; Fiorenza, A. Preparation of fused aryl 2-aminothiazoles. Gazz. Chim. Ital. 1946, 76, 215-222.
153. Harbeson, S. L.; Tung, R. D.; Liu, J. F.; Masse, C. E. Preparation of deuterated dioxabicyclooctyl hydroxyethylamino sulfonamides as HIV protease inhibitors. WO Patent 127272A2, 2010.
154. Katritzky, A. R.; Drewniak, M.; Aurrecoechea, J. M. N-Monomethylation of primary amines via intermediate benzothiazol-2(3H)-imines. J. Chem. Soc., Perkin Trans. 1 1987, 2539-2541.
155. Bryce, M. R.; Fleckenstein, E.; Huenig, S. Synthesis and redox behavior of highly conjugated bis(benzo-1,3-dithiole) and bis(benzothiazole) systems containing aromatic linking groups: model systems for organic metals. J. Chem. Soc., Perkin Trans. 2 1990, 1777-1783.
156. Nomoto, Y.; Takaj, H.; Ohno, T.; Kubo, K. Studies on cardiotonic agents. VI. Synthesis of novel 4,5-dihydro-3(2H)-pyridazinone derivatives carrying some benzoheterocycles at the 6-position. Chem. Pharm. Bull. 1991, 39, 352-357.
157. Monge, A.; Pena, M. d. C.; Palop, J. A.; Caldero, J. M.; Roca, J.; Garcia, E.; Romero, G.; del, R. J.; Lasheras, B. Synthesis of 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives with 5-HT3 antagonist and 5-HT4 agonist properties. J. Med. Chem. 1994, 37, 1320-1325.
158. Tabarrini, O.; Stevens, M.; Cecchetti, V.; Sabatini, S.; Dell'Uomo, M.; Manfroni, G.; Palumbo, M.; Pannecouque, C.; De, C. E.; Fravolini, A. Structure Modifications of 6-Aminoquinolones with Potent Anti-HIV Activity. J. Med. Chem. 2004, 47, 5567-5578.
159. Surleraux, D. L. N. G.; De, K. H. A.; Verschueren, W. G.; Pille, G. M. E.; Maes, L. J. R.; Peeters, A.; Vendeville, S.; De, M. S.; Azijn, H.; Pauwels, R.; De, B. M.-P.; King, N. M.; Prabu-Jeyabalan, M.; Schiffer, C. A.; Wigerinck, P. B. T. P. Design of HIV-1 Protease Inhibitors Active on Multidrug- Resistant Virus. J. Med. Chem. 2005, 48, 1965-1973.
160. Shibata, K.; Mitsunobu, O. Preparation of 1,4-dienes from 2-(2- hydroxyalkylseleno)benzothiazoles by the reaction involving selenium → oxygen azaaromatic ring rearrangement. Bull. Chem. Soc. Jpn. 1992, 65, 3163-3173.
161. D'Amico, J. J.; Tung, C. C.; Walker, L. A. Nitrosoanilines. J. Am. Chem. Soc. 1959, 81, 5957-5963.
162. Jain, M. L.; Soni, R. P. Synthesis of heterocycles: synthesis of naphtho[4,5- b]thiazolo[2,3-a][1,2,4]triazepines. Heterocycles 1981, 16, 1077-1080.
163. Hrobarikova, V.; Hrobarik, P.; Gajdos, P.; Fitilis, I.; Fakis, M.; Persephonis, P.; Zahradnik, P. Benzothiazole-based fluorophores of donor-n-acceptor-ndonor type displaying high two-photon absorption. J. Org. Chem. 2010, 75, 3053-3068.
164. Blaise, C.; Bouanane, A.; Lochon, P.; Neel, J. New heterocyclic compounds: bis(2-chlorobenzothiazoles). Synthesis. Characterization. Bull. Soc. Chim. Fr. 1976, 1843-1844.
165. Singh, J. V. s-Triazolo[5,4-b]naphtho[2,1-d]thiazole. Novel heterocyclic system. J. Indian Chem. Soc. 1974, 51, 443-444.
166. Stewart, G. W.; Baxter, C. A.; Cleator, E.; Sheen, F. J. A mild and efficient one-pot synthesis of 2-aminated benzoxazoles and benzothiazoles. J. Org. Chem. 2009, 74, 3229-3231.
167. Bonk, J. D.; Amos, D. T.; Olson, S. J. Convenient One-Pot Synthesis of Sulfonamides from Thiols using Trichloroisocyanuric Acid. Synth. Commun. 2007, 37, 2039-2050.
168. Mizuno, Y.; Adachi, K.; Nakamura, K. Benzothiazoles. XII. Studies on the reaction between 2-chlorobenzothiazoles and compounds possessing reactive methylene groups. Pharm. Bull. 1953, 1, 319-322.
169. Ramurthy, S.; Aikawa, M.; Amiri, P.; Costales, A.; Hashash, A.; Jansen, J. M.; Lin, S.; Ma, S.; Renhowe, P. A.; Shafer, C. M.; Subramanian, S.; Sung, L.; Verhagen, J. Design and synthesis of 5,6-fused heterocyclic amides as Raf kinase inhibitors. Bioorg. Med. Chem. Lett. 2011, 21, 3286-3289.
170. Ueno, Y.; Kojima, A.; Okawara, M. A convenient and general synthesis of alkane sulfinic acids. Chem. Lett. 1984, 13, 2125-2128.
171. Katritzky, A. R.; Aurrecoechea, J. M.; Vazquez, d. M. L. M. Carbanions derived from 2-(alkylthio)benzothiazoles. A novel a-lithiomethyl mercaptan synthon for mercaptomethylation. J. Chem. Soc., Perkin Trans. 1 1987, 769-774.
172. Katritzky, A. R.; Ghiviriga, I.; Cundy, D. J. The diverse reactivity of (benzothiazol-2-ylthio)(benzotriazol-1-yl)methane. Heterocycles 1994, 38, 1041-1052.
173. Katritzky, A. R.; Kuzmierkiewicz, W.; Aurrecoechea, J. M. Reactions of (benzothiazol-2-ylthio)(trimethylsilyl)methane. A general method for amercaptoalkylation by alkylation and alkylative desilylation. J. Org. Chem. 1987, 52, 844-849.
174. Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Palladium-catalyzed crosscoupling of benzylzinc reagents with methylthio N-heterocycles: a new coupling reaction with unusual selectivity. Synlett 2000, 905-907.
175. Koshiba, T.; Miyazaki, T.; Tokuyama, H.; Fukuyama, T. Palladiumcatalyzed coupling of N-heteroaryl sulfides with organozinc reagents. Heterocycles 2009, 77, 233-239.
176. Metzger, A.; Melzig, L.; Despotopoulou, C.; Knochel, P. Pd-Catalyzed Cross-Coupling of Functionalized Organozinc Reagents with Thiomethyl- Substituted Heterocycles. Org. Lett. 2009, 11, 4228-4231.
177. Melzig, L.; Metzger, A.; Knochel, P. Room temperature cross-coupling of highly functionalized organozinc reagents with thiomethylated Nheterocycles by nickel catalysis. J. Org. Chem. 2010, 75, 2131-2133.
178. Begouin, J.-M.; Rivard, M.; Gosmini, C. Cobalt-catalyzed C-SMe bond activation of heteroaromatic thioethers. Chem. Commun. 2010, 46, 5972-5974.
179. Calo, V.; Scordari, F.; Nacci, A.; Schingaro, E.; D'Accolti, L.; Monopoli, A. Stereoselective Synthesis of Tetrasubstituted 2,3-Dihydrofurans by One-Step Cyclization of b-Ketosulfides of Benzothiazole and Aldehydes in Ionic Liquids. J. Org. Chem. 2003, 68, 4406-4409.
180. Krayushkin, M. M.; Stoyanovich, F. M.; Zolotarskaya, O. Y.; Murav'ev, I. V.; Martynkin, A. Y.; Uzhinov, B. M. Photochromic dihetarylethenes. 10. Photochromic 1,2-bis[2-(benzothiazol-2-yl)-3-thienyl]- and 1,2-bis[2- (benzothiazol-2-yl)benzothiophen-3-yl]ethenes. Russ. Chem. Bull. 2001, 50, 2420-2423.
181. Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. Stereochemistry of the olefin formation from anti and syn heterocyclic β-hydroxy sulfones. Bull. Soc. Chim. Fr. 1993, 130, 336-537.
182. Russell, G. A.; Tashtoush, H.; Ngoviwatchai, P. Alkylation of b-substituted styrenes by a free radical addition-elimination sequence. J. Am. Chem. Soc. 1984, 106, 4622-4623.
183. Carreon, J. R.; Mahon, K. P.; Kelley, S. O. Thiazole Orange-Peptide Conjugates: Sensitivity of DNA Binding to Chemical Structure. Org. Lett. 2004, 6, 517-519.
184. Ikeda, S.; Kubota, T.; Yuki, M.; Okamoto, A. Exciton-Controlled Hybridization-Sensitive Fluorescent Probes: Multicolor Detection of Nucleic Acids. Angew. Chem., Int. Ed. 2009, 48, 6480-6484.
185. Metzger, J.; Larive, H.; Dennilauler, R.; Baralle, R.; Gaurat, C. Behavior and reactivity of heterocyclic ammonium compounds in the synthesis of cyanine and carbocyanine dyes. II. Behavior of 2-methylbenzothiazolium salts in a protonic medium. Bull. Soc. Chim. Fr. 1964, 2868-2878.
186. Florio, S.; Capriati, V.; Gallo, A.; Cohen, T.; Chen, F.; Kulinski, T. Reductive lithiation of sulfur-containing heterocycles with aromatic radical anions: synthetic applications. Gazz. Chim. Ital. 1996, 126, 351-357.
187. Akiba, K.; Shiraishi, H.; Inamoto, N. Direct synthesis of 2,2-diaryl-3-methyl- 2,3-dihydrobenzothiazoles from 3-methyl-2,3-dihydrobenzothiazole-2-thione and some mechanistic aspects. Bull. Chem. Soc. Jpn. 1979, 52, 156-159.
188. Booker, S.; D'Angelo, N.; D'Amico, D. C.; Kim, T.-S.; Liu, L.; Meagher, K.; Norman, M. H.; Panter, K.; Schenkel, L. B.; Smith, A. L.; Tamayo, N. A.; Whittington, D. A.; Xi, N.; Yang, K. Preparation of 2-aminobenzothiazole derivatives as phosphoinositide 3-kinase (PI3 kinase) modulators. WO Patent 017822A2, 2009.
189. Fitzjohn, S.; Robinson, M. P.; Turnbull, M. D.; Smith, A. M.; Salmon, R.; Taylor, R. Benzoxazole and bezothiazole derivatives. WO Patent 9406782A1, 1994.
190. Liebeskind, L. S.; Srogl, J. Heteroaromatic Thioether-Boronic Acid Cross- Coupling under Neutral Reaction Conditions. Org. Lett. 2002, 4, 979-981.
191. Modha, S. G.; Trivedi, J. C.; Mehta, V. P.; Ermolatev, D. S.; Van, d. E. E. V. An Expeditious Route toward Pyrazine-Containing Nucleoside Analogues. J. Org. Chem. 2011, 76, 846-856.
192. Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Copper(I)-Promoted Palladium-Catalyzed Cross-Coupling of Unsaturated Tri-n-butylstannane with Heteroaromatic Thioether. Org. Lett. 2003, 5, 803-805.
193. Egi, M.; Liebeskind, L. S. Heteroaromatic Thioether-Organostannane Cross- Coupling. Org. Lett. 2003, 5, 801-802.
194. Hurd, C. D.; Gershbein, L. L. Reactions of mercaptans with acrylic and methacrylic acid derivatives. J. Am. Chem. Soc. 1947, 69, 2328-2335.
195. Harman, M. W. Mercapto nitriles. US Patent 2413917, 1947.
196. Halasa, A. F.; Smith, G. E. P. Michael and Mannich reactions with benzothiazole-2-thiol. J. Org. Chem. 1971, 36, 636-641.
197. D'Amico, J. J.; Suba, L.; Ruminski, P. G. Synthesis of 3-(2- benzothiazolylthio)propanenitrile and related products. J. Heterocycl. Chem. 1986, 23, 1629-1635.
198. Romani, S.; Moroder, L.; Bovermann, G.; Wuensch, E. On the use of fivemembered heterocycles in peptide chemistry. Synthesis 1985, 738-742.
199. Hu, Y.; Chen, Z.-C.; Le, Z.-G.; Zheng, Q.-G. Organic Reactions in Ionic Liquids: An Efficient Method for Selective S-Alkylation of 2- Mercaptobenzothia(xa)zole with Alkyl Halides. Synth. Commun. 2004, 34, 2039-2046.
200. Dalal, D. S.; Pawar, N. S.; Mahulikar, P. P. Synthesis of 2- Mercaptobenzothiazole and of 2-Mercapto-Benzimidazole Derivatives Using Polymer-Supported Anions. Org. Prep. Proced. Int. 2005, 37, 539-546.
201. Ramanatham, V. K.; Kotha, V. S. R. S. K.; Kotarkonda, R. G. Facile synthesis of 2-(substitutedbenzylsulfanyl)-benzothiazoles and their antimicrobial activity screening. J. Heterocycl. Chem. 2005, 42, 153-156.
202. Nishio, T.; Shiwa, K. Acylation and alkoxycarbonylation of benzoxazoline- 2-thione and benzothiazoline-2-thione. Heterocycles 2004, 62, 313-324.
203. Shah, S. T. A.; Khan, K. M.; Martinez Heinrich, A.; Voelter, W. An alternative approach towards the syntheses of thioethers and thioesters using CsF-Celite in acetonitrile. Tetrahedron Lett. 2002, 43, 8281-8283.
204. Narkhede, H. P.; More, U. B.; Dalal, D. S.; Pawar, N. S.; More, D. H.; Mahulikar, P. P. Fly-Ash-Supported Synthesis of 2-Mercaptobenzothiazole Derivatives under Microwave Irradiation. Synth. Commun. 2007, 37, 573-577.
205. Duarte, A.; Cunico, W.; Pereira, C. M. P.; Flores, A. F. C.; Freitag, R. A.; Siqueira, G. M. Ultrasound promoted synthesis of thioesters from 2- mercaptobenzoxa(thia)zoles. Ultrason. Sonochem. 2010, 17, 281-283.
206. Deligeorgiev, T.; Kaloyanova, S.; Lesev, N.; Vaquero, J. J. An easy and fast ultrasonic selective S-alkylation of hetaryl thiols at room temperature. Ultrason. Sonochem. 2010, 17, 783-788.
207. Zhu, T.-H.; Zhu, X.; Xu, X.-P.; Chen, T.; Ji, S.-J. Ultrasound irradiation promoted catalyst-free construction of formamidine framework using isocyanide as building blocks. Tetrahedron Lett. 2011, 52, 2771-2775.
208. Wan, Y.; Xue, Q.; Cao, L.; Shen, G. Preparation and performance of novel lubricating oil additives derived from 2-mercaptobenzothiazole. J. Am. Oil Chem. Soc. 1996, 73, 1205-1206.
209. Love, B. E. Facile Synthesis of N-Dialkylaminomethyl-Substituted Heterocycles. J. Org. Chem. 2006, 72, 630-632.
210. Khodair, A. I.; Al-Masoudi, N. A.; Gesson, J.-P. A New Approach to the Synthesis of Benzothiazole, Benzoxazole, and Pyridine Nucleosides as Potential Antitumor Agents. Nucleos. Nucleot. Nucleic Acids 2003, 22, 2061-2076.
211. Varma, R. S.; Nobles, W. L. N-Substituted benzothiazoline-2-thiones. J. Pharm. Sci. 1969, 58, 497-498.
212. Misra, R. S.; Barthwal, J. P.; Parmar, S. S.; Brumleve, S. J. Substituted benzoxazole/benzothiazole-2-thiones. Interrelation between anticonvulsant activity and inhibition of nicotinamide adenine dinucleotide-dependent oxidations and monoamine oxidase. J. Pharm. Sci. 1974, 63, 401-404.
213. Braig, A.; Meier, H. R.; Leppard, D. G.; Wasson, R. C.; Phillips, E. Preparation of 3-(hydroxybenzyl)-2(3H)-benzothiazolethiones as corrosion inhibitors. EP Patent 259254A1, 1988.
214. Furuichi, N.; Hara, H.; Osaki, T.; Nakano, M.; Mori, H.; Katsumura, S. Stereocontrolled Total Synthesis of a Polyfunctional Carotenoid, Peridinin. J. Org. Chem. 2004, 69, 7949-7959.
215. Besson, T.; Al, N. M.; Viaud, M. C.; Rollin, P. Mitsunobu thiofunctionalization. Part 2. An expedient synthesis of azaheterocycle/ thiosugar hybrids. Synth. Commun. 1990, 20, 1631-1639.
216. Chochrek, P.; Wicha, J. 1,3-Chirality transfer by fragmentation of allylsulfinic acids: a diastereoselective approach to vinyl bromides related to trans-hydrindane or trans-decalin. Eur. J. Org. Chem. 2007, 2534-2542.
217. Allendoerfer, N.; Es-Sayed, M.; Nieger, M.; Braese, S. Novel aromatic fluoro olefins via fluoro-Julia-Kocienski olefination. Synthesis 2010, 3439-3448.
218. Reed, F. P.; Robertson, A.; Sexton, W. A. Reactions of benzothiazole derivatives. II. The conversion of 1-alkylthiobenzothiazoles into 1-thio-2- alkyl-1,2-dihydrobenzothiazoles. J. Chem. Soc. 1939, 473-476.
219. Moore, C. G.; Waight, E. S. 814. 2-Mercaptobenzothiazole derivatives. Part II. The thermal decomposition and isomerisation of 2-alkyl- and 2-alkenylthiobenzothiazoles and 3-alkyl- and 3-alkenyl-2-thiobenzothiazolines. J. Chem. Soc. 1952, 4237-4251.
220. Fry, D. J.; Kendall, J. D. 374. The formation and fission of quaternary salts of heterocyclic bases containing reactive alkylthio-groups. J. Chem. Soc. 1951, 1716-1722.
221. Morgan, K. J. 165. The alkylation of mercaptobenzothiazole. J. Chem. Soc. 1958, 854-858.
222. Brzezinska, E.; Ternay, A. L. Disulfides. 1. Syntheses Using 2,2'- Dithiobis(benzothiazole). J. Org. Chem. 1994, 59, 8239-8244.
223. Souers, A. J.; Rosenquist, A.; Jarvie, E. M.; Ladlow, M.; Feniuk, W.; Ellman, J. A. Optimization of a somatostatin mimetic via constrained amino acid and backbone incorporation. Bioorg. Med. Chem. Lett. 2000, 10, 2731-2733.
224. Calo, V.; Lopez, L.; Pesce, G. A simple three-step synthesis of b,bdisubstituted acrylates. J. Organomet. Chem. 1988, 353, 405-409.
225. Elliott, J. M.; Castro, J. L.; Chicchi, G. G.; Cooper, L. C.; Dinnell, K.; Hollingworth, G. J.; Ridgill, M. P.; Rycroft, W.; Kurtz, M. M.; Shaw, D. E.; Swain, C. J.; Tsao, K.-L.; Yang, L. 4,4-Disubstituted cyclohexylamine NK1 receptor antagonists I. Bioorg. Med. Chem. Lett. 2002, 12, 1755-1758.
226. Watanabe, Y.; Araki, T.; Ueno, Y.; Endo, T. A radical deoxygenation of secondary alcohols to hydrocarbons by use of tributyltin hydride. Tetrahedron Lett. 1986, 27, 5385-5388.
227. Semmelhack, M. F.; Epa, W. R.; Cheung, A. W. H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. Palladium-Promoted Synthesis of Ionophore Antibiotics. Strategy and Assembly of the Homochiral Tetrahydrofuran and Tetrahydropyran Portions of Tetronomycin. J. Am. Chem. Soc. 1994, 116, 7455-7456.
228. Mukaiyama, T.; Matsueda, R.; Suzuki, M. Peptide synthesis via the oxidation-reduction condensation by the use of 2,2'-dipyridyldisulfide as an oxidant. Tetrahedron Lett. 1970, 11, 1901-1904.
229. Ito, K.; Iida, T.; Fujita, T.; Tsuji, S. A Simple Method for the Synthesis of Amides by Use of 2,2'-Dibenzothiazolyl Disulfide as an Oxidant. Synthesis 1981, 287.
230. Murakami, M.; Minamida, R.; Itami, K.; Sawamura, M.; Ito, Y. Palladiumcatalysed asymmetric [4 + 2] cycloaddition of vinylallene with 1,3-diene. Chem. Commun. 2000, 2293-2294.
231. Kanwar, S.; Sharma, S. D. Use of 2,2'-Dibenzothiazolyl Disulfide- Triphenylphosphine and Lawesson's Reagent in the Cyclization of beta- Amino Acids. Bull. Chem. Soc. Jpn. 2006, 79, 1748-1752.
232. Roblin, R. O.; Clapp, J. W. The Preparation of Heterocyclic Sulfonamides1. J. Am. Chem. Soc. 1950, 72, 4890-4892.
233. Diltz, S.; Aguirre, G.; Ortega, F.; Walsh, P. J. Synthesis of chiral heteroaromatic tetradentate sulfonamide based ligands. Tetrahedron: Asymmetry 1997, 8, 3559-3562.
234. Vedejs, E.; Lin, S.; Klapars, A.; Wang, J. Heteroarene-2-sulfonyl Chlorides (BtsCl; ThsCl): Reagents for Nitrogen Protection and >99% Racemization- Free Phenylglycine Activation with SOCl2. J. Am. Chem. Soc. 1996, 118, 9796-9797.
235. Vedejs, E.; Kongkittingam, C. Solution-Phase Synthesis of a Hindered NMethylated Tetrapeptide Using Bts-Protected Amino Acid Chlorides: Efficient Coupling and Methylation Steps Allow Purification by Extraction. J. Org. Chem. 2000, 65, 2309-2318.
236. Bornholdt, J.; Felding, J.; Clausen, R. P.; Kristensen, J. L. Ring Opening of Pymisyl-Protected Aziridines with Organocuprates. Chem. Eur. J. 2010, 16, 12474-12480.
237. Vedejs, E.; Kongkittingam, C. A Total Synthesis of (-)-Hemiasterlin Using N-Bts Methodology. J. Org. Chem. 2001, 66, 7355-7364.
238. Grunewald, G. L.; Seim, M. R.; Bhat, S. R.; Wilson, M. E.; Criscione, K. R. Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase. Biorg. Med. Chem. 2008, 16, 542-559.
239. Marsault, E.; Hoveyda, H. R.; Peterson, M. L.; Saint-Louis, C.; Landry, A.; Vézina, M.; Ouellet, L.; Wang, Z.; Ramaseshan, M.; Beaubien, S.; Benakli, K.; Beauchemin, S.; Déziel, R.; Peeters, T.; Fraser, G. L. Discovery of a New Class of Macrocyclic Antagonists to the Human Motilin Receptor. J. Med. Chem. 2006, 49, 7190-7197.
240. Lee, H.; Jeon, J. H.; Lim, J. C.; Choi, H.; Yoon, Y.; Kim, S. K. Peptide Nucleic Acid Synthesis by Novel Amide Formation. Org. Lett. 2007, 9, 3291-3293.
241. Wright, S. W.; Hallstrom, K. N. A Convenient Preparation of Heteroaryl Sulfonamides and Sulfonyl Fluorides from Heteroaryl Thiols. J. Org. Chem. 2006, 71, 1080-1084.
242. Bornholdt, J.; Fjære, K. W.; Felding, J.; Kristensen, J. L. Heterocyclic pentafluorophenyl sulfonate esters as shelf stable alternatives to sulfonyl chlorides. Tetrahedron 2009, 65, 9280-9284.
243. Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. A direct synthesis of olefins by the reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or 2'-alkenyl- or benzylsulfonyl]benzothiazoles. Tetrahedron Lett. 1991, 32, 1175-1178.
244. Baudin, J. B.; Hareau, G.; Julia, S. A.; Lorne, R.; Ruel, O. Stereochemistry of direct olefin formation from carbonyl compounds and lithiated heterocyclic sulfones. Bull. Soc. Chim. Fr. 1993, 130, 856-878.
245. Warren, L. A.; Smiles, S. CLXXI.-Dehydro-2-naphtholsulphone. J. Chem. Soc. 1930, 1327-1331.
246. Blakemore, P. R. The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585.
247. Aïssa, C. Mechanistic Manifold and New Developments of the Julia- Kocienski Reaction. Eur. J. Org. Chem. 2009, 1831-1844.
248. Plesniak, K.; Zarecki, A.; Wicha, J. The Smiles Rearrangement and the Julia-Kocienski Olefination Reaction. Top. Curr. Chem. 2007, 275, 163-250.
249. Zajc, B.; Kumar, R. Synthesis of fluoroolefins via Julia-Kocienski olefination. Synthesis 2010, 1822-1836.
250. Blakemore, P. R.; Ho, D. K. H.; Nap, W. M. Ethyl (benzothiazol-2- ylsulfonyl)acetate: a new reagent for the stereoselective synthesis of α,β- unsaturated esters from aldehydes. Org. Biomol. Chem. 2005, 3, 1365-1368.
251. Manjunath, B. N.; Sane, N. P.; Aidhen, I. S. New reagent for convenient access to the α,β-unsaturated N-methoxy-N-methyl-amide functionality by a synthesis based on the Julia olefination protocol. Eur. J. Org. Chem. 2006, 2851-2855.
252. Kapeller, D. C.; Kocienski, P. J. 2-Benzothiazolyl propargyl sulfides: versatile precursors for enantiopure allens, E-α,β-unsaturated ketones and Zsulfonylalkenes. Synthesis 2010, 3811-3821.
253. Ueno, Y.; Yadav, L. D. S.; Okawara, M. Carbon-carbon bond formation via phosphine-initiated cleavage of b-oxosulfides. Chem. Lett. 1983, 831-834.
254. Nielsen, M.; Jacobsen, C. B.; Holub, N.; Paixao, M. W.; Joergensen, K. A. Asymmetric organocatalysis with sulfones. Angew. Chem. Int. Ed. 2010, 49, 2668-2679.
255. Nielsen, M.; Borch, J. C.; Paixao, M. W.; Holub, N.; Jorgensen, K. A. Asymmetric Organocatalytic Formal Alkynylation and Alkenylation of α,β- Unsaturated Aldehydes. J. Am. Chem. Soc. 2009, 131, 10581-10586.
256. Holub, N.; Jiang, H.; Paixao, M. W.; Tiberi, C.; Joergensen, K. A. An Unexpected Michael-Aldol-Smiles Rearrangement Sequence for the Synthesis of Versatile Optically Active Bicyclic Structures by Using Asymmetric Organocatalysis. Chem. Eur. J. 2010, 16, 4337-4346.
257. Jacobsen, C. B.; Lykke, L.; Monge, D.; Nielsen, M.; Ransborg, L. K.; Jorgensen, K. A. An asymmetric organocatalytic approach towards allylic amines and β-keto amino compounds. Chem. Commun. 2009, 6554-6556