Reductive formation of 1,5-benzothiazepines

Heterocycles

Volumn 68, Issue 7, 2006, Pages 1319-1324

  Lévai, Albert ^a   Tóth, Gábor ^b,c   Gondos, Tímea ^b,c   Jeko, József ^d   Brahmbhatt, D I ^e  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^c Drug Research Institute Ltd   (Hungary)

^d Department of Agricultural Sciences and Environmental Management   (Hungary)

^e SARDAR PATEL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746920563     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-06-10702     Document Type: Article

References (39)

1. Oxazepines and Thiazepines, 44. For Part 43, see. Kéki S., Nagy L., Deák Gy., Lévai A., and Zsuga M. Rapid Commun. Mass Spectrom. 19 (2005) 1263
2. Geismann T.A. The Chemistry of Flavonoid Compounds (1962), Pergamon Press
3. Harborne J.B. The Flavonoids: advances in research since 1980 (1988), Chapman and Hall, London
4. Harborne J.B. The Flavonoids: advances in research since 1986 (1993), Chapman and Hall, London
5. Khan M.S.Y., and Sharma P. Indian J. Chem. 34B (1995) 237
6. Brahmbhatt D.I., Raolji G.B., Pandya S.U., and Pandya U.R. Indian J. Chem. 38B (1999) 212
7. Miky J.A.A., and Farrag A.A. Indian J. Chem. 36B (1997) 357
8. Essawy A.I., Elkady M., and Mohamed A.Y. Indian J. Chem. 19B (1980) 567
9. van den Goorbergh J.A.M., van der Steeg M., and van der Gen A. Synthesis (1984) 859
10. Dimitrova E., and Anghelova Y. Synth. Commun. 16 (1986) 1195
11. van den Goorbergh J.A.M., van der Steeg M., and van der Gen A. Synthesis (1987) 314
12. Yagodinets P.I., Skripskaya O.V., Chernyuk I.N., and Shevchuk M.I. Zh. Obschch. Khim. 61 (1991) 1856
13. Djudjic R., and Trkovnik M. Croat. Chem. Acta 63 (1990) 13
14. Prashant A., Srinivas Rao S., Chowdary K.S., and Krishnan V.S.H. Heterocycl. Commun. 7 (2001) 61
15. Mulwad V.V., and Pawar R.B. Indian J. Chem. 42B (2003) 2091
16. Ried W., and Marx W. Chem. Ber. 90 (1957) 2683
17. Stephens W.D., and Field L. J. Org. Chem. 24 (1959) 1576
18. Hideg-Hankovszky O., and Hideg K. Acta Chim. Acad. Sci. Hung. 68 (1971) 403
19. Lévai A., and Bognár R. Acta Chim. Acad. Sci. Hung. 88 (1976) 293
20. Lévai A., and Bognár R. Acta Chim. Acad. Sci. Hung. 92 (1977) 415
21. Lévai A. Pharmazie 34 (1979) 439
22. Lévai A., Bognár R., and Kajtár J. Acta Chim. Acad. Sci. Hung. 103 (1980) 27
23. Lévai A. Pharmazie 36 (1981) 449
24. Mane R.A., and Ingle D.B. Indian J. Chem. 21B (1982) 973
25. Orlov V.D., Kolos N.N., and Ruzhinckaya N.N. Khim. Geterotsikl. Soedin. (1983) 1638
26. Gupta A.K., Singh V.K., and Pant U.C. Indian J. Chem. 22B (1983) 1057
27. Jadhav K.P., and Ingle D.B. Indian J. Chem. 22B (1983) 180
28. Pant U.C., Gaur B.S., and Chugh M. Indian J. Chem. 27B (1988) 752
29. Lévai A. Pharmazie 44 (1989) 317
30. Lévai A. Heterocycl. Commun. 5 (1999) 359
31. Swellen R.H., Allam Y.A., and Nawwar G.A.M. Z. Naturforsch. 54b (1999) 1197
32. Katritzky A.R., Rogovoy B.V., Chassaing C., Vedensky V., Forood B., Flatt B., and Nakai H. J. Heterocyclic Chem. 37 (2000) 1655
33. Lévai A. J. Heterocyclic Chem. 37 (2000) 199
34. Kodomari M., Noguchi T., and Aoyama T. Synth. Commun. 34 (2004) 1783
35. Nagarapu L., Narendar R., and Sucheta K. Heterocycl. Commun. 9 (2003) 35
36. Representative Experimental Procedure. Synthesis of Compound 8d: A mixture of 1d (1.38 g, 5.0 mmol), 2-aminothiophenol (1.80 g, 15.0 mmol), toluene (50 mL) and acetic acid (5.0 mL) was refluxed for 6 h, then the solvent was evaporated under reduced pressure and the residue was crystallized from methanol to afford compound (8d) (Scheme 1).
37. Pretsch E., Tóth G., Munk M.E., and Badertscher M. Computer-Aided Structure Elucidation, Spectra Interpretation and Structure Generation (2002), Wiley-VCH, London
38. 13C NMR: δ = 52.7 (C-2), 36.0 (C-3), 159.5 (C-4), 85.2 (C-3′), 27.3 (C-4′); MS (m/z) 419; Yield 57%, mp 170-171 °C.
39. Y. A., Ueda T., and Imoto T. J. Biochem. 115 (1994) 52