tert-butyl-N-chlorocyanamide: A novel and versatile reagent in organic synthesis

Synlett

Volumn , Issue 19, 2007, Pages 2937-2951

  Kumar, Vinod ^a   Kaushik, Mahabir P ^a  

^a DEFENCE RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

Addition reactions; Chlorinations; N chloro compounds; Oxidations; tert butyl N chlorocyanamide

Indexed keywords

2 ISOXAZOLINE DERIVATIVE; ALKANEDIOL DERIVATIVE; ALKENE DERIVATIVE; CHLORIDE; CHLORINE; CYANAMIDE; MUSTARD GAS; OXIME DERIVATIVE; REAGENT; SULFIDE; SULFOXIDE; TERT BUTYL N CHLOROCYANAMIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; OXIDATION; PHOTOLYSIS; SYNTHESIS; WATER TREATMENT;

EID: 37249079616     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992369     Document Type: Article

References (117)

1. For reviews covering N-chloro compounds, see: (a) Kowalski, P.; Mitka, K.; Ossowska, K.; Kolarska, Z. Tetrahedron 2005, 61, 1933.
2. (b) Kolvari, E.; Ghorbani-Choghamarani, A.; Salehi, P.; Shirini, F.; Zolfigol, M. A. J. Iran. Chem. Soc. 2007, 4, 126; and references cited therein.
3. (c) Koval, I. V. Russ. J. Org. Chem. (Engl. Transl.) 2002, 38, 301.
4. Virgil, S. C. In Encyclopedia of Reagents for Organic Synthesis, Vol. 7; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995, 1205.
5. Kelly, R. C. In Encyclopedia of Reagents for Organic Synthesis, Vol. 7; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995, 1208.
6. Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452.
7. Liu, K.-C.; Shelton, B. R.; Howe, R. K. J. Org. Chem. 1980, 45, 3916.
8. Kim, K. S.; Cho, I. H.; Yoo, B. K.; Song, Y. H.; Hahn, C. S. J. Chem. Soc., Chem. Commun. 1984, 762.
9. Lee, G. A. Synthesis 1982, 508.
10. Hiegel, G. A. In Encyclopedia of Reagents for Organic Synthesis, Vol. 7; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995, 1272.
11. Tilstam, U.; Weinmann, H. Org. Process Res. Dev. 2002, 4, 384.
12. Juenge, E. C.; Beal, D. A. Tetrahedron Lett. 1968, 9, 5819.
13. Cohen, T.; Kosarych, Z.; Suzuki, K.; Yu, L.-C. J. Org. Chem. 1985, 50, 2965.
14. Walters, T. R.; Zajac, W. W. Jr.; Woods, J. M. J. Org. Chem. 1991, 56, 316.
15. Hiegel, G. A.; Nalbandy, M. Synth. Commun. 1992, 22, 1589.
16. Tilstam, U.; Harre, M.; Heckrodt, T.; Weinmann, H. Tetrahedron Lett. 2001, 42, 5385.
17. De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041.
18. De Luca, L.; Giacomelli, G.; Simonetta, M.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999.
19. Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. Synlett 2001, 1641.
20. Zolfigol, M. A.; Choghamarani, A. G.; Hazarkhani, H. Synlett 2002, 1002.
21. Zolfigol, M. A.; Ghaemi, E.; Madrakian, E. Synlett 2003, 191.
22. Wengert, M.; Sanseverino, A. M.; de Mattos, M. C. S. J. Braz. Chem. Soc. 2002, 13, 700.
23. Mendonca, G. F.; Sanseverino, A. M.; de Mattos, M. C. S. Synthesis 2003, 45.
24. Ye, J.; Wang, Y.; Chen, J.; Liang, X. Adv. Synth. Catal. 2004, 346, 691.
25. Acharya, J.; Gupta, A. K.; Shakya, P. D.; Kaushik, M. P. Tetrahedron Lett. 2005, 46, 5293.
26. Rao, Z.; Zhang, X.; Baeyens, W. R. G. Talanta 2002, 57, 993.
27. Khazaei, A.; Manesh, A. A. Synthesis 2005, 1929.
28. Skibinska, M.; Zahn, F. A.; Czarnocka, A.; Lewenstein, W. Acta Pol. Pharm. 1969, 6, 25.
29. Campbell, M. M.; Johnson, G. Chem. Rev. 1978, 78, 65.
30. Brenner, D. H. In Synthetic Reagents, Vol. 6; Pizey, J. S., Ed.; Wiley: New York, 1985, 9.
31. Barton, D. H. R.; Britten-Kelly, M. R.; Ferreira, D. J. Chem. Soc., Perkin Trans. 1 1978, 1090.
32. Sharpless, K. B.; Hori, T.; Truesdale, L. K.; Dietrich, C. O. J. Am. Chem. Soc. 1976, 98, 269.
33. Sharpless, K. B.; Singer, S. P. J. Org. Chem. 1976, 41, 2504.
34. Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 451.
35. Sharpless, K. B.; Chong, A. O.; Oshima, K. J. Org. Chem. 1976, 41, 177.
36. Rubin, A. E.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1997, 36, 2637.
37. Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 280.
38. Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2813.
39. Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1997, 36, 1483.
40. Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207.
41. Reddy, K. L.; Dress, K. R.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 3667.
42. Dawn, H.-S.; Pitman, I. H.; Young, T. H. S. J. Pharm. Sci. 2006, 59, 955.
43. Kevin, I.; Milburn, B.; Guly, D. J.; Cox, B.; Procopiou, P. A. Org. Lett. 2003, 5, 3313.
44. Farook, N. A. M.; Kanagaraj, M. E-J. Chem. 2004, 1, 1.
45. Farook, N. A. M.; Mahendran, G. R. E-J. Chem. 2004, 1, 57.
46. Farook, N. A. M.; Kumar, R. S. E-J. Chem. 2004, 1, 65.
47. Farook, N. A. M.; Murugesan, A. E-J. Chem. 2004, 1, 73.
48. Farook, N. A. M.; Dameem, G. A. S.; Kanagaraj, M. E-J. Chem. 2004, 1, 132.
49. Hunter, R.; Caira, M.; Stellenboom, N. J. Org. Chem. 2006, 71, 8268.
50. Katritzky, A. R.; Vakulenko, A. V.; Jain, R. ARKIVOC 2003, (xiv), 131.
51. Hiremath, R. C.; Mayanna, S. M.; Venkatasubramanian, N. J. Sci. Ind. Res. 1990, 49, 122.
52. Hiremath, R. C.; Jagadeesh, R. V.; Puttaswamy; Mayanna, S. M. J. Chem. Sci. 2005, 117, 333.
53. Channegowda, C.; Mayanna, S. M. Microchim. Acta 1990, 271.
54. Gupta, A. K.; Acharya, J.; Pardasani, D.; Dubey, D. K. Tetrahedron Lett. 2007, 48, 767.
55. Dubey, D. K.; Malhotra, R. C.; Vaidyanathaswamy, R.; Vijayraghavan, R. J. Org. Chem. 1993, 64, 8301.
56. Vijayraghavan, R.; Kumar, P.; Dubey, D. K.; Singh, R. Biomed. Environ. Sci. 2002, 15, 25.
57. Shakya, P. D.; Dubey, D. K.; Pardasani, D.; Palit, M.; Gupta, A. K. J. Chem. Res. 2005, 821.
58. Sathe, M.; Karade, H.; Kaushik, M. P. Chem. Lett. 2007, 36, 996.
59. Neale, R. S.; Marcus, N. L. J. Org. Chem. 1969, 34, 1808.
60. Ghosh, S.; Baul, S. Synth. Commun. 2001, 31, 2783.
61. Kumar, V.; Kaushik, M. P. unpublished results.
62. (a) Patel, B. K. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed., Vol. 7; Kroschwitz, J. I.; Howe-Grant, M., Eds.; John Wiley & Sons: New York, 2003, 736.
63. (b) Rodd's Chemistry of Carbon Compounds, 2nd ed., Vol. 1C; Coffey, S., Ed.; Elsevier: Amsterdam, 1965.
64. (c) Kukushkin, V. Y.; Pombeiro, A. J. L. Chem. Rev. 2002, 102, 1771.
65. (d) Michelin, R. A.; Mozzon, M.; Bertani, R. Coord. Chem. Rev. 1996, 147, 299.
66. (e) Ray, P. Chem. Rev. 1961, 61, 313.
67. Kumar, V. Synlett 2005, 1638.
68. Benders, P. H.; Hackman, I. T. Recl. Trav. Chim. Pays-Bas 1972, 91, 343.
69. (a) See also ref. 59
70. (b) Banks, R. E.; Burling, E. D. J. Chem. Soc. 1965, 6077.
71. Yang, Y. C.; Baker, J. A.; Ward, J. R. Chem. Rev. 1992, 92, 1729.
72. (a) Kruglyak, Y. L.; Landau, M. A.; Leibovskaya, G. A.; Martynov, I. V.; Saltykova, L. I. Zh. Obshch. Khim. 1971, 41, 2338.
73. (b) Cecherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Tetrahedron Lett. 1980, 39, 4385.
74. (c) Sabuni, M.; Kresz, G.; Braun, H. Tetrahedron Lett. 1984, 25, 5377.
75. (d) Martynov, I. V.; Chepakova, L. A.; Brel, V. K.; Sokolov, V. B. Zh. Obshch. Khim. 1986, 56, 2020.
76. (e) See also ref. 12
77. (f) Tordeux, M.; Boumizane, K.; Wakselman, C. J. Org. Chem. 1993, 58, 1939.
78. (g) Wang, Y. C.; Lu, T. M.; Elango, S.; Lin, C. K.; Tsai, C. T.; Van T, H. Tetrahedron: Asymmetry 2002, 13, 691.
79. Kumar, V.; Kaushik, M. P. Tetrahedron Lett. 2005, 46, 8121.
80. (a) Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410.
81. (b) Kanemasa, S.; Tsuge, O. Heterocycles 1990, 30, 719.
82. (c) Esipenko, A. A.; Samarai, L. I. Russ. Chem. Rev. (Engl. Transl.) 1993, 62, 1097.
83. (d) Caramella, P.; Grunanger, P. Nitrile Oxides and Imines, In 1,3-Dipolar Cycloaddition Chemistry, Vol. 1; Padwa, A., Ed.; Wiley: New York, 1984, Chap. 3, 291.
84. (e) Torssell, K. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH: New York, 1988.
85. (f) Grünanger, P.; Vita-Finzi, P. Isoxazoles, In The Chemistry of Heterocyclic Compounds, Part 1, Vol. 49; Wiley: New York, 1991.
86. (a) Shankar, B. B.; Yang, D. Y.; Girton, S.; Ganguly, A. K. Tetrahedron Lett. 1998, 39, 2447.
87. (b) Sammelson, R. E.; Ma, T.; Galietta, L. J. V.; Verkman, A. S.; Kurth, M. J. Bioorg. Med. Chem. Lett. 2003, 13, 2509.
88. (c) Bal, G.; der Venken, P. V.; Antonov, D.; Lambeir, A.-M.; Grellier, P.; Croft, S. L.; Augustyns, K.; Haemers, A. Bioorg. Med. Chem. Lett. 2003, 13, 2875.
89. Kumar, V.; Kaushik, M. P. Tetrahedron Lett. 2006, 47, 1457.
90. (a) Eto, M. In Organophosphorus Pesticides: Organic and Biological Chemistry; CRC: Cleveland OH, 1974, 18.
91. (b) Van Wazer, J. R. Phosphorus and its Compounds, Vol. II; Interscience: New York, 1961.
92. (c) Engel, R. Chem. Rev. 1977, 77, 349.
93. (d) Kosolapoff, G. M. In Organic Phosphorus Compounds, Vol. 6; Wiley-Interscience: New York, 1950, 503.
94. Kumar, V.; Kaushik, M. P. Chem. Lett. 2006, 35, 312.
95. (a) Holland, H. L. Chem. Rev. 1988, 88, 473.
96. (b) Block, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 1135.
97. (c) Durst, T. In Comprehensive Organic Chemistry, Vol. 3; Barton, D.; Ollis, W. D., Eds.; Pergamon: Oxford, 1979, 121.
98. (d) Carreno, M. C. Chem. Rev. 1995, 95, 1717.
99. (e) Solladie, G. Synthesis 1981, 185.
100. (f) Ikemoto, N.; Schrieber, S. L. J. Am. Chem. Soc. 1990, 112, 9657.
101. (g) Berkowitz, D. B.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1992, 114, 4518.
102. Kumar, V.; Kaushik, M. P. Chem. Lett. 2005, 34, 1230.
103. (a) Papirmeister, B.; Feister, A. J.; Robinson, S. I.; Ford, R. D. Medical defense against mustard gas: Toxic mechanism and medical implications; CRC: Boca Raton FL, 1991, 359.
104. (b) Pechura, C. M.; Rail, D. P. The health effects of mustard gas and lewisite; National Academic Press: Washington DC, 1993, 428.
105. Kumar, V.; Kaushik, M. P. Synth Commun. 2006, 36, 2385.
106. Davis, F. A.; Jenkins, R. Jr.; Yocklovich, S. G. Tetrahedron Lett. 1978, 19, 5171.
107. Chemistry of Bivalent Sulfur, Reid, E. E., Ed.; Chemical Publishing Co.: New York, 1960, Chap. 5.
108. Anslow, J. R.; Karnofsky, D. A.; Valjager, B.; Smith, H. W. J. Pharmacol. Exp. Ther. 1948, 93, 1.
109. (a) Oae, S. Organic Sulfur Chemistry: Structure and Mechanism, Vol. 1; CRC: Boca Raton FL, 1991.
110. (b) Cremlyn, R. J. An Introduction to Organosulfur Chemistry; John Wiley & Sons: New York, 1996.
111. (c) Ogawa, A.; Nishiyama, Y.; Kambe, N.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1987, 28, 3271.
112. (d) Bischoff, L.; David, C.; Martin, L.; Meudal, H.; Roques, B.-P.; Fournié-Zaluski, M.-C. J. Org. Chem. 1997, 62, 4848.
113. Kumar, V.; Kaushik, M. P. Bull. Chem. Soc. Jpn. 2007, in press.
114. (a) Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph 186: Washington DC, 1990.
115. (b) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic: New York, 1981.
116. (c) Sheldon, R. A.; Arends, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774.
117. Kumar, V.; Kaushik, M. P., unpublished results.