Azidotrimethylsilane-mediated Schmidt rearrangement of 2-aryl-1,2,3,4-tetrahydro-1-methylsulfonyl-4-quinolones: Non-regioselectivity of carbon migration

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 23, 1999, Pages 3477-3482

  Mphahlele, Malose J ^a  

^a SEFAKO MAKGATHO HEALTH SCIENCES UNIVERSITY   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002527235     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906449d     Document Type: Article

References (25)

1. J. T. Sharp, Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, vol. 7, p. 608.
2. G. Marc and S. Pecar, Synth. Commun., 1998, 28, 1143 and references cited therein.
3. P. T. Kaye and R. D. Whittal, S. Afr. J. Chem., 1991, 44, 30;
4. P. T. Kaye and R. D. Whittal, S. Afr. J. Chem., 1991, 44, 56.
5. P. T. Kaye and M. J. Mphahlele, J. Chem. Res., 1994, (S) 62; (M) 367.
6. P. T. Kaye and M. J. Mphahlele, Synth. Commun., 1995, 25, 1495.
7. R. B. English, P. T. Kaye, M. J. Mphahlele and R. D. Whittal, J. Chem. Res., 1995, (S) 388; (M) 2319;
8. R. B. English, P. T. Kaye and M. J. Mphahlele, S. Afr. J. Chem, 1997, 50, 55;
9. M. J. Mphahlele and P. T. Kaye, Magn. Reson. Chem., 1998, 36, 69.
10. S. Daya, P. T. Kaye and M. J. Mphahlele, Med. Sci. Res., 1996, 24, 137.
11. D. Msiti, F. Gatta and R. Landi-Vittory, J. Heterocycl. Chem., 1971, 81, 231.
12. K. H. Wunsch, K. H. Stahnke and A. Ehlers, Chem. Ber., 1970, 103, 2302.
13. I. W. J. Still, M. T. Thomas and A. M. Clish, Can. J. Chem., 1975, 53, 276.
14. P. T. Kaye, M. J. Mphahlele and M. E. Brown, J. Chem. Soc., Perkin Trans. 2, 1995, 835.
15. D. Evans and I. M. Lokhart, J. Chem. Soc., 1965, 4806.
16. J. March, in Advanced Organic Chemistry: Reaction Mechanism and Structure, 4th edn., Wiley, New York, 1992, p. 509.
17. M. J. Mphahlele and M. R. C. Mabusela, S. Afr. J. Chem., in the press.
18. A. C. Gelebe and P. T. Kaye, S. Afr. J. Chem., 1992, 45, 109.
19. (a) U. T Bhalerao and G. Thyagarajan, Can. J. Chem., 1968, 46, 3367;
20. (b) D. Msiti and V. Rimatori, Ann. 1st. Super. Sanita, 1973, 9, 150;
21. (c) A. Levai and R. Bogna, Acta Chim. Acad. Sci. Hung., 1978, 97, 77;
22. (d) A. Levai, Acta Chim. Acad. Sci. Hung., 1980, 104, 385;
23. (e) A. Levai, T. Timor, L. Frank and S. Hosztafi, Heterocycles, 1992, 34, 1523.
24. R. Bach and G. J. Wolber, J. Org. Chem., 1982, 47, 239.
25. J. A. Donnelly and D. F. Farrell, Tetrahedron, 1990, 46, 885.