Silica gel-promoted synthesis of 3,4,5-triaryltetrahydro-1,4-thiazine derivatives from β,β′-dichloro sulfides and aromatic amines

Tetrahedron Letters

Volumn 46, Issue 47, 2005, Pages 8105-8108

  Mihara, Masatoshi ^a   Ito, Takatoshi ^a   Ishino, Yoshio ^a   Oderaotoshi, Yoji ^b   Minakata, Satoshi ^b   Komatsu, Mitsuo ^b  

^a OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

, Dichloro sulfides; Amines; Silica gel; Sulfur dichloride; Tetrahydrothiazine derivatives

Indexed keywords

ALKENE DERIVATIVE; AROMATIC AMINE; BETA,BETA' DICHLORO SULFIDE DERIVATIVE; CHLORINE DERIVATIVE; SILICA GEL; SULFUR DERIVATIVE; SULFUR DICHLORIDE; TETRAHYDRO 1,4 THIAZINE DERIVATIVE; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 27144538219     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.119     Document Type: Article

References (35)

1. G.H. Posner Angew. Chem., Int. Ed. Engl. 17 1978 487 496
2. A. McKillop, and D.W. Young Synthesis 1979 401 422
3. A. McKillop, and D.W. Young Synthesis 1979 481 500
4. P. Laszlo Preparative Chemistry Using Supported Reagents 1987 Academic Press San Diego
5. V.A. Basiuk Russ. Chem. Rev. 64 1995 1003 1019
6. G.W. Kabalka, and R.M. Pagni Tetrahedron 53 1997 7999 8065
7. A.K. Banerjee, M.S.L. Mimó, and W.J.V. Vegas Russ. Chem. Rev. 70 2001 971 990
8. M. Mihara, Y. Ishino, S. Minakata, and M. Komatsu Synlett 2002 1526 1528
9. M. Mihara, Y. Ishino, S. Minakata, and M. Komatsu Synthesis 2003 2317 2320
10. S. Kotha, K. Mandal, A.C. Deb, and S. Banerjee Tetrahedron Lett. 45 2004 9603 9605
11. G. Bartoli, M. Bartolacci, A. Giuliani, E. Marcantoni, M. Massaccesi, and E. Torregiani J. Org. Chem. 70 2005 169 174
12. G.J. Reddy, D. Latha, C. Thirupathaiah, and K.S. Rao Tetrahedron Lett. 46 2005 301 302
13. M. Mihara, Y. Ishino, S. Minakata, and M. Komatsu J. Org. Chem. 70 2005 5320 5322
14. S. Minakata, M. Mihara, N. Sugoh, and M. Komatsu Heterocycles 47 1998 133 137
15. M. Mihara, Y. Ishino, S. Minakata, and M. Komatsu Synthesis 2001 2397 2400
16. E.J. Corey, and E. Block J. Org. Chem. 31 1966 1663 1668
17. E.D. Weil, K.J. Smith, and R.J. Gruber J. Org. Chem. 31 1966 1669 1679
18. W.H. Mueller Angew. Chem., Int. Ed. Engl. 8 1969 482 492
19. R.C. Fort Jr., M.H. Stahl, and A.F. Sky J. Org. Chem. 52 1987 2396 2399
20. M. Komatsu, H. Ogawa, M. Mohri, and Y. Ohshiro Tetrahedron Lett. 31 1990 3627 3630
21. M. Komatsu, M. Mohri, S. Kume, and Y. Ohshiro Heterocycles 32 1991 659 662
22. A. Converso, K. Burow, A. Marzinzik, K.B. Sharpless, and M.G. Finn J. Org. Chem. 66 2001 4386 4392
23. A. Converso, P.-L. Saaidi, K.B. Sharpless, and M.G. Finn J. Org. Chem. 69 2004 7336 7339
24. H.T. Clarke J. Chem. Soc. 101 1912 1583 1590
25. W.E. Lawson, and E.E. Reid J. Am. Chem. Soc. 47 1925 2821 2836
26. W.F. Hart, and J.B. Niederl J. Am. Chem. Soc. 68 1946 714 715
27. F. Lautenschlaeger J. Org. Chem. 34 1969 3998 4001
28. M.J. Cook A.J. Boulton A. McKillop Comprehensive Heterocyclic Chemistry Vol. 3 1984 Pergamon Press Oxford 987
29. R.J. Stoodley A.R. Katritzky A.J. Boulton Advanced in Heterocyclic Chemistry Vol. 24 1979 Academic Press New York 293 361
30. M.J. Cook A.J. Boulton A. McKillop Comprehensive Heterocyclic Chemistry Vol. 3 1984 Pergamon Press Oxford 1037 1038
31. M.R. Barbachyn, D.K. Hutchinson, S.J. Brickner, M.H. Cynamon, J.O. Kilburn, S.P. Klemens, S.E. Glickman, K.C. Grega, S.K. Hendges, D.S. Toops, C.W. Ford, and G.E. Zurenko J. Med. Chem. 39 1996 680 685
32. E. Kumazawa, K. Hirotani, S.C. Burford, K. Kawagoe, T. Miwa, I. Mitsui, and A. Ejima Chem. Pharm. Bull. 45 1997 1470 1474
33. O.B. Helfrich, and E.E. Reid J. Am. Chem. Soc. 42 1920 1208 1232
34. +, 53), 181 (100), 104 (17), 77 (22).
35. 3, 20 mL). The filtered and washed silica gel was used in the next run. The work-up and purification follow the methods described in the general procedure.