Oxazepines and thiazepines, 36. Diastereoselective sulfoxidation of 2,3- dihydro-1,5-benzothiazepin-4(5H)-ones by dimethyldioxirane

Heterocycles

Volumn 51, Issue 1, 1999, Pages 85-94

  Patonay, Tamás ^a   Adam, Waldemar ^b   Jeko, József ^c   Kövér, Katalin E ^a   Lévai, Albert ^a   Németh, Márta ^a   Peters, Karl ^d  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c Alkaloida Chemical Company Ltd   (Hungary)

^d MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZEPINE DERIVATIVE; OXAZEPINE DERIVATIVE; SULFONE; SULFOXIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032816226     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-98-8353     Document Type: Article

References (46)

1. Part 35: A. Lévai, Heterocycl. Comm., 1997, 3, 211.
2. (a) A. Lévai, Trends Heterocycl. Chem., 1995, 4, 51;
3. (b) A. Chimini, R. Gitto, S. Grasso, A.M. Monforte, and M. Zappala, 'Advances in Heterocyclic Chemistry: Annelated 1,5-Benzothiazepines', Vol. 63, ed. by A.R. Katritzky, Academic Press, Inc., San Diego, 1995, pp. 61-101.
4. (a) J. Krapcho, E.R. Spitzmiller, and C.F. Turk, J. Med Chem., 1963, 6, 544;
5. (b) J. Krapcho and C. F. Turk, J. Med. Chem., 1966, 9, 191;
6. (c) J. Krapcho, C.F. Turk, and J.J. Piala, J. Med. Chem., 1968, 11, 361.
7. (a) H. Kugita, H. Inoue, M. Ikezaki, and S. Takeo, Chem. Pharm. Bull., 1970, 18, 2028;
8. (b) H. Kugita, H. Inoue, M. Ikezaki, M. Konda, and S. Takeo, Chem. Pharm. Bull., 1970, 18, 2284;
9. (c) H. Kugita, H. Inoue, M. Ikezaki, M. Konda, and S. Takeo, Chem. Pharm. Bull., 1971, 19, 595.
10. K.P. Jadhav and D.B. Ingle, Indian J. Chem., 1983, 22B, 180.
11. (a) V. Nacci, G. Filacchioni, and G.C. Porretta, Farmaco - Ed. Sci., 1972, 27, 1003;
12. (b) V. Nacci, G. Filacchioni, G.C. Porretta, G. Stefanovich, and A. Guaitani, Farmaco - Ed. Sci., 1973, 28, 494.
13. R.J. DeVita, W.R. Schoen, G.A. Doldouras, M. H. Fisher, M. J. Wyvratt, K. Cheng, W.W.-S. Chan, B.S. Butler, and R. G. Smith, Biorg. Med. Chem. Lett., 1995, 5, 1281.
14. J.W. Shiler, R. Sorcek, S. Jacober, C. Miao, P.W. Mui, D. McNeil, and A. S. Rosenthal, Biorg. Med. Chem. Lett., 1993, 3, 773.
15. G. Campiani, V. Nacci, I. Fiorini, M.P. De Filippis, A. Garofalo, G. Greco, E. Novellino, S. Altamura, and L. Di Renzo, J. Med. Chem., 1996, 39, 2672.
16. (a) J. Slade, J.L. Stanton, D. Ben-David, and G.C. Mazzenga, J. Med. Chem., 1985, 28, 1517;
17. (b) K. Itoh, M. Kori, Y. Inada, K. Nishikawa, Y. Kawamatsu, and H. Sugihara, Chem. Pharm. Bull., 1986, 34, 1128.
18. C. Giordano and A. Restelli, Tetrahedron: Asymmetry, 1991, 2, 785.
19. (a) K.-H. Wünsch, K.-H. Stanke, and A. Ehlers, Chem. Ber., 1970, 103, 2302;
20. (b) I.W.J. Still, M.T. Thomas, and A.M. Clish, Can. J. Chem., 1975, 53, 276.
21. M. Miyazaki, T. Iwakuma, and T. Tanaka, Chem. Pharm. Bull., 1978, 26, 2889.
22. G. Puzicha, A. Lévai, and G. Snatzke, Monatsh. Chem., 1990, 121, 293.
23. A. Lévai, Acta Chim. Acad. Sci. Hung., 1979, 102, 141.
24. R. Breitschuh and D. Seebach, Synthesis, 1992, 1170.
25. M. Wilhelm and P. Schmidt, Helv. Chim. Acta, 1970, 53, 1697.
26. A. Lévai, Arch. Pharm. (Weinheim) 1992, 325, 721.
27. (a) W. Adam, R. Curci, and J.O. Edwards, Acc. Chem. Res., 1989, 22, 205;
28. (c) R.W. Murray, Chem. Rev., 1989, 89, 1187;
29. (c) W. Adam, R. Curci, L. Hadjiarapoglou, and R. Mello, 'Organic Peroxides: Dioxiranes: 3-Membered Ring Cyclic Peroxides', ed. by W. Ando, Wiley-Interscience, Chichester, 1992, pp. 195-219;
30. (d) W. Adam and L. Hadjiarapoglou, 'Topics in Current Chemistry: Dioxiranes: Oxidation Chemistry Made Easy', Vol. 164, ed. by W.A. Herrmann, 1993, pp. 45-62.
31. (a) W. Adam and D. Golsch, Chem. Ber., 1994, 127, 1111;
32. (b) W. Adam, D. Golsch, and F.C. Görth, Chem. Eur. J., 1996, 2, 255;
33. (c) W. Adam and D. Golsch, J. Org. Chem., 1997, 62, 115.
34. (a) R.W. Murray, R. Jeyaraman, and M. K. Pillay, J. Org. Chem., 1987, 52, 740;
35. (b) J.J.W. McDouall, J. Org. Chem., 1992, 57, 2861;
36. (c) E.L. Clennan and K. Yang, J. Org. Chem., 1993, 58, 4504;
37. (d) F.P. Ballistreri, G.A. Tomaselli, R.M. Toscano, M. Bonchio, V. Conte, and F. DiFuria, Tetrahedron Lett., 1994, 35, 8041.
38. W. Adam, D. Golsch, L. Hadjiarapoglou, A. Lévai, Cs. Nemes, and T. Patonay, Tetrahedron, 1994, 50, 13113.
39. The cis prefix refers to the isomer in which the sulfoxide oxygen and the alkyl/aryl group at the 2 position are on the same side of the heteroring. The trans-2b has the (1R*,2S*), while the trans-2c,d have the (1R*,2R*) relative configurations, the difference due to the change in the priority of the substituents at the C-2 atom.
40. Software package VAMP 5.0: G. Rauhut, J. Chandrasekhar, A. Alex, T. Steinke, and T. Clark, University of Erlangen-Nürnberg, Germany, 1993.
41. U. Zoller, 'The Chemistry of Functional Groups: The Synthesis of Sulphones, Sulphoxides and Cyclic Sulfides', ed. by S. Patai, and Z. Rappoport, Wiley, Chichester, 1994.
42. H. Duddeck, M. Kaiser, and A. Lévai, Liebigs Ann. Chem., 1985, 869.
43. W. Adam, J. Bialas, and L. Hadjiarapoglou, Chem. Ber., 1991, 124, 2377.
44. (a) A. Lévai, Pharmazie, 1980, 35, 680;
45. (b) H. Duddeck and A. Lévai, Pharmazie, 1983, 38, 827.
46. 14 but the diastereomeric purity of the product was not stated.