Ring opening of epoxides and aziridines with sodium azide using Oxone® in aqueous acetonitrile: A highly regioselective azidolysis reaction1

Synthesis

Volumn , Issue 15, 2002, Pages 2254-2258

  Sabitha, Gowravaram ^a   Babu, R Satheesh ^a   Reddy, M Shashi Kumar ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Azides; Aziridines; Epoxides; Oxone ; Regioselectivity

Indexed keywords

ACETONITRILE; NITROGEN COMPOUNDS; SODIUM COMPOUNDS;

RING OPENINGS;

SYNTHESIS (CHEMICAL);

ACETONITRILE; AMINE; AZIDE; AZIRIDINE DERIVATIVE; EPOXIDE; OXIDIZING AGENT; POTASSIUM PEROXYSULFATE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; TEMPERATURE;

EID: 0036412425     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34848     Document Type: Article

References (37)

1. IICT communication No. 03/02/02.
2. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737.
3. (a) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
4. (b) Coleman, R. S. Synlett 1998, 1031.
5. (a) Erden, I. In Comprehensive Heterocyclic Chemistry, Vol. IA; Padwa, A., Ed.; Pergamon Press: Oxford, 1996, Chap. 1.03.
6. (b) Bartok, M.; Lang, K. L. In Chemistry of Heterocyclic Compounds, Vol. 42; Weissberger, A.; Taylor, E. C., Eds.; Wiley: NewYork, 1985, Part 3, 1.
7. (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
8. (b) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry, Vol. 7; Iwowski, W., Ed.; Pergamon: Oxford, 1984, 47-93.
9. (c) Kasai, M.; Kono, M. Synlett 1992, 778.
10. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
11. (e) Rayner, C. M. Synlett 1997, 11
12. The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: New York, 1971.
13. Chandrasekhar, M.; Sekar, G.; Singh, V. K. Tetrahedron Lett. 2000, 41, 10079.
14. Bergmeir, S. C. Tetrahedron 2000, 56, 2561.
15. (a) Rogers, G. A.; Parsons, S. M.; Nilsson, D. C.; Bahr, L. M.; Kornreich, W. D.; Kaufman, R.; Jacobs, R. S.; Kirtman, B. J. Med. Chem. 1989, 32, 1217.
16. (b) Chng, B. L.; Ganesan, A. Bioorg. Med. Chem. Lett. 1997, 7, 1511.
17. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297.
18. (a) Coe, D. M.; Myers, P. L.; Parry, D. M.; Roberts, S. M.; Storer, R. J. Chem. Soc., Chem. Commun. 1990, 151.
19. (b) Jacobs, G. A.; Tino, J. A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955.
20. Hou, J. W.; Dai, L.-X. J. Org. Chem. 2000, 65, 1344.
21. (a) Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Eur. J. Org. Chem. 1998, 5, 1675.
22. (b) Blandy, C.; Choukroun, R.; Gervais, D. Tetrahedron Lett. 1983, 24, 4189.
23. (c) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768.
24. (d) For a recent review, see: Paterson, I.; Berrisford, D. J. In Organic Synthesis Highlights, Vol. III; Mulzer, J.; Waldmann, H., Eds.; Wily-VCH: Weinheim, 1998.
25. (e) Muller, E. P. Helv. Chim. Acta 1882, 65, 1617.
26. (f) Schneider, C. Synlett 2000, 12, 1840.
27. (g) Li, Z.; Fernandez, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611.
28. Onaka, M.; Sugita, K.; Izumi, Y. J. Org. Chem. 1989, 54, 1116.
29. (a) Saito, S.; Nishikawa, T.; Yokoyama, Y.; Yamashita, S. Tetrahedron Lett. 1989, 30, 4153.
30. (b) Saito, S.; Nishikawa, T.; Yokoyama, Y.; Mariwake, T. Tetrahedron Lett. 1990, 31, 221.
31. Tamami, B.; Mahdev, H. Tetrahedron Lett. 2001, 42, 8721.
32. Leung, W.-H.; Yu, M.-T.; Wu, M.-C.; Yeung, L.-L. Tetrahedron Lett. 1996, 37, 891.
33. Ferraris, D.; Drury, W. J. III; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568.
34. Sabitha, G.; Babu, R. S.; Rajkumar, M.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2001, 42, 3955.
35. Sabitha, G.; Satheesh Babu, R.; Shashikumar, M; Yadav, J. S. New. J. Chem., 2002, in press.
36. Sabitha, G.; Syamala, M.; Yadav, J. S. Org. Lett. 1999, 1, 1701.
37. Sabitha, G.; Babu, R. S.; Rajkumar, M.; Yadav, J. S. Org. Lett. 2002, 4, 343; and references cited therein.