Supramolecular synthesis of selenazoles using selenourea in water in the presence of β-cyclodextrin under atmospheric pressure

Journal of Organic Chemistry

Volumn 72, Issue 5, 2007, Pages 1849-1851

  Narender, M ^a   Reddy, M Somi ^a   Kumar, V Pavan ^a   Reddy, V Prakash ^a   Nageswar, Y V D ^a   Rao, K Rama ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC PRESSURE; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL); UREA;

CYCLODEXTRIN; SELENAZOLES; SELENOUREA;

KETONES;

BETA CYCLODEXTRIN; BROMINE DERIVATIVE; SELENAZOLE DERIVATIVE; SELENIUM DERIVATIVE; UREA; WATER;

ARTICLE; ATMOSPHERIC PRESSURE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; TEMPERATURE;

BETA-CYCLODEXTRINS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; ORGANOSELENIUM COMPOUNDS; SPECTROPHOTOMETRY, INFRARED; UREA; WATER;

EID: 33847609737     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062421q     Document Type: Article

References (49)

1. (a) Caşsar, Z.; Majcen-Le, A.; Marechal; Lorey, D. New J. Chem. 2003, 27, 1622.
2. (b) Koketsu, M.; Ishihara, H. Curr. Org. Chem. 2003, 7, 175.
3. (c) Duddeck, H.; Bradenahl, R.; Stefaniak, L.; Jazwinski, J.; Kamienski, B. Magn. Resonance Chem. 2001, 39, 709.
4. (d) Archer, S.; McGarry, R. J. Heterocyclic Chem. 1982, 19, 1245.
5. (a) Park, Y.-J.; Koketsu, M.; Kim, J. M.; Yeo, J.-H.; Ishihara, H.; Lee, K.-G.; Kim, S. Y.; Kim, C.-K. Biol. Pharm. Bull. 2003, 26, 1657.
6. (b) Koketsu, M.; Choi, S. Y.; Ishihara, H.; Lim, B. O.; Kim, H.; Kim, S. Y. Chem. Pharm. Bull. 2002, 50, 1594.
7. (c) Li, H.; Hallows, W. H.; Punzi, J. S.; Marquez, V. E.; Carell, H. L.; Pankiewicz, K. W.; Watanabe, K. A.; Goldstein, B. M. Biochemistry 1994, 33, 23.
8. (d) Goldstein, B. M.; Leary, J. F.; Farley, B. A.; Marquez, V. E.; Levy, P. C.; Rowley, P. T. Blood 1991, 78, 593.
9. (e) Burling, F. T.; Goldstein, B. M. J. Am. Chem. Soc. 1992, 114, 2313.
10. (a) Goldstein, B. M.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc. 1990, 112, 8265 and references cited therein.
11. (b) Shafiee, A.; Khashayarmanesh, Z.; Kamal, F. J. Sci., Islamic Repub. Iran 1990, 1, 11.
12. (c) Shafiee, A.; Shafaati, A.; Khamench, B. H. J. Heterocycl. Chem. 1989, 26, 709.
13. (d) For cancerostatic activity of 1,3-selenazoles, see: Srivastava, P. C.; Robins, R. K. J. Med. Chem. 1983, 26, 445.
14. (e) Also see: Shafiee, A.; Mazloumi, A.; Cohen, V. J. J. Heterocycl. Chem. 1979, 16, 1563.
15. Sekhiguchi, A.; Nishina, A.; Kimura, H.; Fukumoto, R.-H.; Koichi, K.; Ishihara, H.; Koketsu, M. Chem. Pharm. Bull. 2005, 53, 1439.
16. (a) Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: London, 1996; Vols. 1-11.
17. (b) Back, T. G. Organoselenium Chemistry: A Practical Approach; Oxford University Press: Oxford, 1999.
18. (c) Wirth, T. Organoselenium Chemistry. Modern Developments in Organic Synthesis; Springer: Berlin, 2000.
19. (d) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408.
20. (a) Larsen, R. 1,3-Selenazoles. In Comprehensive Heterocyclic Chemistry II; Kartritzky, A., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996; Vol. 3, Chapter 8.
21. (b) Koketsu, M.; Nada, F.; Ishihara, H. Synthesis 2002, 195.
22. (c) Kaminski, R.; Glass, R. S.; Skowronska, A. Synthesis 2001, 1308.
23. (d) Koketsu, M.; Fukuta, Y.; Ishihara, H. Tetrahedron Lett. 2001, 42, 6333.
24. (e) Zhang, P.-F.; Chen, Z.-C. Synthesis 2000, 9, 1219.
25. (f) Maeda, H.; Kambe, N.; Sonoda, N.; Fujiwara, S.-I.; Shinike, T. Tetrahedron 1997, 53, 13667.
26. (g) Lai, L.-L.; Reid, D. H. Synthesis 1993, 870.
27. (h) Ogawa, A.; Miyake, J. I.; Karasaki, Y.; Murai, S.; Sonoda, N. J. Org. Chem. 1985, 50, 384.
28. (i) Cohen, V. I. Synthesis 1978, 668.
29. Geisler, K.; Pfeiffer, W.-D.; Müller, C.; Nobst, E.; Bulka, E.; Langer, P. Synthesis 2003, 1215.
30. (a) Koketsu, M.; Kogami, M.; Ando, H.; Ishihara, H. Synthesis 2006, 0031.
31. (b) Geisler, K.; Kunzler, A.; Below, H.; Bulka, E.; Pfeiffer, W.-D.; Langer, P. Synthesis 2004, 0097.
32. (c) Koketsu, M.; Imogawa, M.; Mio, T.; Ishihara, H. J. Heterocycl. Chem. 2005, 42, 831.
33. Koketsu, M.; Mio, T.; Ishihara, H. Synthesis 2004, 233.
34. Koketsu, M.; Tanaka, H.; Ishihara, H. Chem. Lett. 2005, 34, 1260.
35. Dictionary of Organic Compounds, 6th ed.; Chapman and Hall: New York, 1995; Vol. 6, p5646.
36. (a) OECD (Organization for Economical Cooperation and Development) Workshop on Sustainable Chemistry, 1998.
37. (b) Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1998.
38. (c) Anastas, P. T.; Williamson, T. C.; Hjeresen, D. L.; Breen, J. J. Promoting Green Chemistry Initiatives, in Environm. Sci. Technol. 1999, 33, 116A-119A.
39. (a) Jaeger, D. A.; Frey, M. R. J. Org. Chem. 1982, 47, 311-315.
40. (b) Jaeger, D. A.; Jamrozik, J.; Golich, T. G.; Clennan, M. W.; Mohebalian, J. J. Am. Chem. Soc. 1989, 111, 3001-3006.
41. (c) Jaeger, D. A.; Sayed, Y. M.; Dutta, A. K. Tetrahedron Lett. 1990, 31, 449-450.
42. (a) Surendra, K.; Krishnaveni, N. S.; Mahesh, A.; Rao, K. R. J. Org. Chem. 2006, 71, 2532.
43. (b) Krishnaveni, N. S.; Surendra, K.; Rao, K. R. Chem. Commun. 2005, 669.
44. (c) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 2058.
45. (d) Krishnaveni, N. S.; Surendra, K.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 2018.
46. Szejtli, J.; Osa, T. In Comprehensive Supramolecular Chemistry; Pergamon Press: New York, 1996; Vol. 3.
47. Geisler, K.; Pfeiffer, W. -D.; Kunzler, A.; Below, H.; Bulka, E.; Langer, P. Synthesis 2004, 875.
48. (a) Demarco, P. V.; Thakkar, A. L. Chem. Commun. 1970, 2.
49. (b) D'Souza, Lipkowitz, K. B. Chem. Rev. 1998, 98, 1741-2076.