Oxidation of N-heterocyclics: A green approach

Journal of Heterocyclic Chemistry

Volumn 44, Issue 6, 2007, Pages 1223-1230

  Sivasubramanian, Ganarajan ^b   Parameswaran, Veembil Ramachandran ^a  

^a ANNAMALAI UNIVERSITY   (India)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; HETEROCYCLIC N OXIDE DERIVATIVE; NITROGEN; OXIDIZING AGENT; OXYGEN; UNCLASSIFIED DRUG;

CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHEMISTRY; ENVIRONMENTAL PROTECTION; GREEN CHEMISTRY; OXIDATION; PHYSICAL CHEMISTRY; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 38949108760     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570440601     Document Type: Review

References (111)

1. Sheldon, R. A.; Kochi, J. K. Metal-Catalysed Oxidation of Organic Compounds, Academic Press, New York, NY, 1981.
2. a) Mijs, W. J.; de Jonge, C. R. H. I. Organic Synthesis by Oxidation With Metal Compounds, Plenum press, New York, NY, 1986.
3. ST, B. M.; Fleming, I. A. Comprehensive Organic Synthesis, Pergamon Press, Oxford, Vol 7, 1991.
4. c) Hudlicky, M. Oxidations in Organic Chemistry, ACS Monograph Ser-186, American Chemical Society, Washington D.C.1990.
5. Anastas, P. T.; Warner, J. C. Green Chemistry, Theory and Practice, Oxford University press, Oxford, 1998.
6. Noyori, R.; Aoki, M.; Sato, K. J. Chem. Soc., Chem. Commun. 2003, 1977-1986.
7. Simandi, L. L.; Ed, Advances in Catalytic Activation of Dioxygen by Metal Complexes, Kulwer Academic, Dordrecht, 1992.
8. Costas, M.; Mehn, M. P.; Hensen, M. P.; Que, L, Jr. Chem. Rev. 2004, 104, 939.
9. Weissermel, K.; Arpe, H. J. Industrial Organic Chemistry, VCH, Weinheim, 1993.
10. Pandiarajan, K. In Synthetic Reagents, pizey, J. S.Ed., Horwood-Wiley, New York, NY, 1985, Vol 6, pp 60.
11. Weselsky, P. Ber. 1871, 4, 613.
12. Katrizky, A.R. Chemistry of Heterocyclic N-oxides, Academic Press, New York, 1971.
13. a) Albini, A.; Pietra, S. Heterocyclic N-oxides, CRC Press, Boca Ranton, 1991.
14. b) Albini, A. Synthesis, 1991, 263.
15. Balazarini, J.; Stevens, M.; De Clercq, E.; Scols, D.; Pannecouque, C.; J. Antimicrob. Chemother. 2005, 55 135,
16. Biochem pharma, 2006, 71, 1122.
17. Balazarini, J.; Keyaerts, E.; Vijgen, L.; Vandermeer, F.; Stevens, M.; Clercq, E. D.; Egberink, H.; Ranst, M. V. J. Antimicrob. Chemother. 2006, 57, 472.
18. Oconnor, C. J.; Sinn, E.; Carlin, R.L. Inorg Chem. 1977, 16, 3314.
19. Roseky, H. W.; Andruh, M. Coord Chem Rev. 2003, 236, 91.
20. a) Palucki, M.; Mc. Cormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457.
21. b) Samsel, G. E.; Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1985, 107, 7606.
22. c) Finney, N. S.; Pospisil, P. J.; Chang, S.; Palucki, M.; Konsler, R. G.; Hansen, B.; Jacobsen, E. N. Angew. Chem Int. Ed. 1997, 36, 1720.
23. d) Berkessel, A.; Fraunekron, M. J. Chem. Soc. Perkin Trans.1 1997, 2265,
24. e) Huges, L.; Smith, G. B.; Liu, J.; Dezeny, G. C.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J.Org Chem., 1997,62, 2222 ().
25. Kilenyi, S. N., In Comprehensive Organic Synthesis, Ley, S. V. Ed., Pergamon Press, Oxford, 1991, Vol 8, pp 661-663.
26. Schrock, R. R. Chem Rev, 2002,102, 145.
27. Basuli, F.; Bailey, B. C.; Tomaszewski, J.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc., 2003, 125, 6052.
28. a) Cummins, C. C.; Schock, R. R.; Davis, W. M. Inorg Chem. 1994, 33, 1448.
29. b) Mullins, S. M.; Ducan, A. P.; Bergman, R. G.; Arnold, J. Inorg Chem. 2001, 40, 6952.
30. c) Sung K. M.; Holm, R. H. J. Am. Chem. Soc. 2001, 123, 1931.
31. Arney, D. S. J.; Burns, C. J. J. Am. Chem. Soc. 1995, 117, 9448.
32. a) Schneider, W. P.; McIintosh, A. V. (upjohn) US Patent 2,769,824,1956; Chem. Abstr. 1957s, 51, 8822e.
33. b) Rheeneen, V. V.; Kelly, R.C., Cha, D. Y.; Tetrahedron Lett. 1976, 17, 1973.
34. c) Day, R.; Matteson, D. Tetrahedron Lett. 1980, 21, 449.
35. Ullmann's Encyclopedia of Industrial Chemistry on CD-ROM, Electronic release, Wiley -VCH, 2002.
36. Chelucci, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Asym. 2004, 15, 1373.
37. Pool, J. A.; Scott, L.; Kiplinger, J. L. J. Am. Chem. Soc. 2005, 127, 1338.
38. Gonzalez, R. L. M.; Villa de, A. L. P.; Montes de C. C.; Gelbard, G. React. Funct. Polym. 2005, 65, 169.
39. Perni, R, B.; Kowalczyk, P. J.; Treasurywala, A. M.; Tetrahedron Lett. 1995, 36, 699.
40. Soscun, H.; Castellano, O.; Bermudez, Y.; Mendoza, C. T.; Marcano, A.; Alvarado, J. J. Mol. Stru. (Theochem). 2002, 592, 19.
41. Prezhdo, V. V.; Vaschenko, E. V.; Prezhdo, O. V.; Puszko, A. J. Mol. Stru. 1998, 47, 127.
42. Dr. Proctor, The World's Best Products at the World's Best Prices (online).
43. Seiborg, K.; Wgheire, G.; Landberg, H. Helv. Chim. Acta. 1969, 52, 789.
44. Evleth, E. Theor. Chim. Acta. 1968, 11, 145.
45. Kulkarni, G. V.; Ray, A. J. Mol. Struct. 1981, 71, 253.
46. Cigniti, M.; Gata, F. Spectrochim. Acta, Part A. 1985, 41 1287.
47. Lutz, B.; Vander Mass, J. H.; Kanthers, J. A. J. Mol. Stru. 1994, 325, 203.;
48. Chem. Abstr. 1995, 122, 133512c.
49. Kunts, S.; Agren.; H.; Minaev, B. F. Thoechem. 1994, 117, 185;
50. Chem. Abstr. 1994, 121, 178999n.
51. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063.
52. Mayazaki, H.; Kubota, T. Bull. Chem. Soc. Jpn. 1977, 45, 78.
53. Maciel, G. E.; McIver, J. W.; Ostund, N. S.; Pope, J. A. J. Am. Chem. Soc. 1970, 92, 4497.
54. Maciel, G. E.; McIver, J. W.; Ostund, N. S.; Pope, J. A. J. Am. Chem. Soc. 1970, 92, 4506.
55. Ernst, L.; Lincoln, D. N.; Wary, V. J. Magn. Resonance. 1976, 21, 115.
56. Contreras, R. H.; Kowalewski, V. J. J. Magn. Resonance. 1980, 39, 291.
57. Yamanaka, H.; Sakamoto, T.; Niitsuma, S. Heterocycles. 1990, 31, 923.
58. Yamanaka, H. Heterocycles. 1992, 33, 3.
59. Kurasawa, Y.; Takada, A.; Kim, H. S. J. Heterocycl. Chem. 1995, 32, 1085.
60. Youssif, S. ARKIVOC. 2001, i, 242, and the references there in.
61. Hartley, F. R.; Supported Metal Complexes, D. Reidel Publishing Company, 1985, pp 1-26.
62. Hodge. P.; Sherrington, D. C. Synthesis and Sepration Using Functionalised Polymers, John Wiley & Sons, New York, NY, 1998.
63. a) Boekelheide, V.; Linn. W. V. J. Am. Chem. Soc. 1954, 76, 1286.
64. b)Brougham, Copper, M. S.; Cummerson, D. A.; Heaney, H.; Thompson, N. Synthesis 1987, 1015.
65. c) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.
66. d) Ferrer, M.; Sanchez-Baeza, F.; Messanguer, A.; Tetrahedron. 1997, 53, 1587.
67. a) Sheldon, R. A. Chemtech. 1994, 38.
68. b) Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998.
69. c) Clark, J. H. Green Chem. 1999, 1, 1.
70. d) De Vos, D. E.; Sels, B. F.; Jacobs, R. A. Adv Catal, 2001, 46, 1.
71. e) Sheldon, R. A. J.Chem.Tech. Biotechnol, 1997, 68, 381.
72. a) Nisiyama, Y.; Nakagawa, Y; Mizuno, N. Angew. Chem. Int. Eds. 2001, 40, 639.
73. b) Thomas, J. M.; Raja, R.; Sankar, G.; Bell, R. G. Acc. Chem. Res. 2001, 34, 191.
74. c) Dobler, C.; Mehltretter, G. M.; Sundermeier, U.; Beller, M. J. Am. Chem. Soc. 2001, 122, 10289.
75. d) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
76. e) Davis, S.; Drago, R. S. J. Chem. Soc., Chem. Commun. 1990, 250.
77. f) David, R. J.; Pugsley, S. J.; Matthew, S. J. Am. Chem. Soc. 2001, 123, 7475.
78. g) Partenheimer, W.; Barton, D. H. R.; Martell, A. E.; Sawyer, D. T. The Activation of Dioxygen and Homogeneous Catalytic Oxidation, Plenum Press, New York, NY, 1993.
79. h) Nishiyama, Y.; Nakagawa, Y.; Mizuno, N. Angew. Chem. 2001, 40, 3639.
80. i) Noboyuki, K.; Yasunari, M.; Nishimura, T.; Umeura, S. J. Org. chem. 2001, 66, 6620.
81. Coperet, C.; Adolfsson, H.; Khunog, T. V.; Andrei, K.; Yudin.; Sharpless, K. B. J. Org. Chem. 1998, 63, 1740.
82. a) Coperet, C.; Adolfsson, H.; Sharpless. K. B. J. Chem. Soc., Chem. Commun. 1997, 1565.
83. b) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6185.
84. Coperet, C.; Adolfsson, H.; Chiang, J. P.; Andrei, K.; Yudin, Sharpless. K. B. Tetrahedron Lett. 1998, 39, 761.
85. Dongre, R. S.; Roa, T. V.; Sharma, B. K.; Sain, B.; Bhatia, V. K. Synth. Commun. 2001, 31(2), 167.
86. Kaneda, K.; Haruna, S.; Imanaka, T.; Hamamoto, M.; Nishiyama, Y.; Ishii. Y. Tetrahedron Lett. 1992, 33, 6827.
87. Choudary, M.; Sudha, Y. Synth. Commun. 1996, 26, 1651.
88. Rao, T. V.; Sain, B.; Kumar, K.; Murthy, P. S.; Roa, T. S. R. P.; Joshi, G. C. Synth. Commun. 1998, 28, 319.
89. Jain. S. L.; Sain, B.; J. Chem. Soc., Chem. Commun. 2002, 1040.
90. Prasad, M. R.; Kamalakar, G.; Madhavi, G.; Kulkarni, S. J.; Raghavan, K. V. J Chem Soc., Chem. Commun. 2000, 17, 1577.
91. Prasad, M. R.; Kamalakar, G.; Madhavi, G.; Kulkarni, S. J.; Raghavan, K. V. J. Mol. Cata. A. 2002, 186, 109.
92. Rout, L.; Punniyamurthy, T. Adv. Synth. Cata. 2005, 347, 1958.
93. Bamoharram, F. F.; Heravi, M. M.; Roshani, M.; Tavakoli. j. Mol. Cata. A. 2006, 252, 219.
94. Winkeljohn, W. R.; Vasquez, P. C.; Strekowski, L.; Baumstark, A. L. Tetrahedron. Lett. 2004, 45, 8295.
95. Dondoni, A.; Modena, G.; Tudesco, Gazz, P. E. Chim.Ital. 1961, 91, 613.
96. a) Bergstad, K.; Backvll, J. E. J. Org. Chem. 1998, 63, 6650.
97. b) Ball, S.; Bruice, T. C. J. Am. Chem. Soc. 1980, 102, 6498.
98. Battioni, T. K. P.; Sanderson, W.; Mansuy, D. Synthesis. 1997, 1387.
99. Armarego, W. L. F. Stereochemistry of Heterocyclic Compounds., Part I: Nitrogen Heterocyclics, John Wiley & Sons, 1997.
100. Chelucci, G.; Murineddu, G.; Pinna, G. A. Tetrahedron: Asymmetry. 2004, 15, 1373.
101. Wasserscheid, T.; Welton, T. Eds. Ionic Liquids in Synthesis. Wiley-VCH Verlag- GmbH & Co. KGaA, 2002.
102. Cornils, B. Org. Process. Res. Dev. 1998, 2, 121.
103. Cornils, H. B.; Herrmann, W. A. Eds. Aqueous-Phase Organometallic Catalysis-Concepts and Applications, VCH, Weinheim, 1998.
104. Wei, W.-L.; Zhu, H.-Y.; Zhao, C.-L.; Haung, M.-Y.; Jiang, Y. Y. React. Funct. Polym. 2004, 59, 33.
105. Zhang, X.; Geng, Y.;Han, B.; Huang, M.-Y.; Jiang, Y. Y. Polym. Adv. Technol. 2001, 12, 642.
106. Haung, K.; Xue, L.; Hu, Y.-C.; Huang, M.-Y.; Jiang, Y.-Y. React. Funct. Polym. 2002, 50, 199.
107. Quignard, F.; Choplin, A.; Domard, A. Langmuir, 2000, 16, 9106.
108. Reddy, K. R.; Kumar, N. S.; Reddy, P. S.; Sreedhar, B.; Kantam, M. L. J. Mol. Cata. A. 2006, 252, 12.
109. Guibal, E. Prog. Polym. Sci. 2005, 30, 71.
110. Hansch. C.; Leo, A. Exploring QSAR Fundamentals and Application in Chemistry and Biology, ACS Professional Reference Book, American Chemical Society, Washington, D.C., 1995.
111. Bromely, S. T.; Catlow, C. R. A.; Maschmeyer, T. Cat Tech. 2003, 7, 164.