Expeditious synthesis of 3,4-dihydro-2H-1λ6-benzo[e] [1,2]thiazine 1,1-dioxides

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 12, 1999, Pages 1730-1733

  Takeuchi, Yoshio ^a   Liu, Zhaopeng ^a   Satoh, Akira ^a   Shiragami, Tomoki ^a   Shibata, Norio ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Annulation; Fluorination; Lithiation; Suitam; fluoroketone

Indexed keywords

3,4 DIHYDRO 2H 1LAMBDA 6 BENZO[E][1,2]THIAZINE 1,1 DIOXIDE; FLUORINE DERIVATIVE; KETONE DERIVATIVE; THIAZINE DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; FLUORINATION; SYNTHESIS;

EID: 0033384395     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.1730     Document Type: Article

References (36)

1. a) Oppolzer W., Wills M., Starkemann C., Bernardinelli G., Tetrahedron Lett., 31, 4117-4120 (1990);
2. b) Oppolzer W., Kingma A. J., Pillai S. K., ibid., 32, 4893-4896 (1991);
3. c) Oppolzer W., Wills M., Kelly M. J., Signer M., Blagg J., ibid., 31, 5015-5018 (1990).
4. Seyden-Penne J. (ed), "Chiral Auxiliaries and Ligands in Asymmetric Synthesis," John Wiley & Sons, New York, 1995.
5. Ahn K. H., Ham C., Kim S.-K., Cho C.-W., J. Org. Chem., 62, 7047-7048 (1997).
6. a) Takeuchi Y., Satoh A., Suzuki T., Kameda A., Dohrin M., Satoh T., Koizumi T., Kirk K. L., Chem. Pharm. Bull., 45, 1085-1088 (1997);
7. b) Kakuda H., Suzuki T., Takeuchi Y., Shiro M., Chem. Commun., 1997, 85-86;
8. c) Takeuchi Y., Liu Z., Suzuki M., Shibata N., J. Fluorine Chem., 97, 65-67 (1999);
9. d) Takeuchi, Y., Suzuki T., Satoh A., Shiragami T., Shibata N., J. Org. Chem., 64, 5708-5711 (1999).
10. a) Sianesi E., Redaelli R., Bertani M., Re P. D., Chem. Ber., 103, 1992-2002 (1970);
11. b) Sianesi E., Redaelli R., Magistretti M. J., Massarani E., J. Med. Chem., 16, 1133-1137 (1973).
12. a) Watanabe H., Hauser C. R., J. Org. Chem., 33, 4278-1279 (1968);
13. b) Watanabe H., Mao C.-L., Barnish I. T., Hauser C. R., ibid., 34, 919-926 (1969).
14. Lombardino J. G., Wiseman E. H., J. Med. Chem., 14, 973-977 (1971).
15. For example a) Zinnes H., Comes R. A., Zuleski F. R., Caro A. N., Shavel J., Jr., J. Org. Chem., 30, 2241-2246 (1965);
16. b) Zinnes H., Comes R. A., Shavel J., Jr., ibid., 31, 162-165 (1966);
17. c) Camoutsis C., Catsoulacos P., J. Heterocyclic Chem., 29, 569-570 (1992);
18. d) Proudfoot J. R., Patel U. R., Dyatkin A. B., J. Org. Chem., 62, 1851-1853 (1997);
19. e) DuPriest M. T., Zinke P. W., Conrow R. E., Kuzmich D., Dantanarayana A. P., Sproull S. J., ibid., 62, 9372-9375 (1997).
20. a) Hermann C. K. F., Campbell J. A., Greenwood T. D., Lewis J. A., Wolfe J. F., J. Org. Chem., 57, 5328-5334 (1992);
21. b) Abramovitch R. A., Smith E. M., Humber M., Purtschert B., Srinivasan P. C., Singer G. M., J. Chem. Soc., Perkin Trans. 1, 1974, 2589-2594.
22. Gensler W. J., Ahmed Q. A., Leeding M. V., J. Org. Chem., 33, 4279-4281 (1968).
23. a) Furin G. G., "New Fluorinating Agents in Organic Synthesis," ed. by German L., Zemskov S., Springer-Verlag, Berlin, 1989, pp. 35-68;
24. b) Furin G. G., Sov. Sci. Rev. B. Chem., 16, 1-140 (1991);
25. c) Purrington S. T., Kagen B. S., Patrick T. B., Chem. Rev., 86, 997-1018 (1986);
26. d) Barton D. H. R., Hesse R. H., Pechet M. M., Toh H. T., J. Chem. Soc., Perkin Trans. 1, 1974, 732-738;
27. e) Barnette, W. E., J. Am. Chem. Soc., 106, 452-454 (1984);
28. f) Singh S., DesMarteau D. D., Zuberi S. S., Witz M., Huang H.-N., ibid., 109, 7194-7196 (1987);
29. g) Differding E., Lang R. W., Helv. Chim. Acta, 72, 1248-1252 (1989);
30. h) Differding E., Ofner H., Synlett., 1991, 187-189;
31. i) Davis F. A., Zhou P., Murphy C. K., Tetrahedron Lett., 34, 3971-3974 (1993);
32. j) Davis F. A., Han W., Murphy C. K., J. Org. Chem., 60, 4730-4737 (1995);
33. k) Cabrera I., Appel W. K., Tetrahedron, 51, 10205-10208 (1995).
34. a) Differding E., Lang R. W., Tetrahedron Lett., 29, 6087-6090 (1988);
35. b) Davis F. A., Han W., ibid., 32, 1631-1634 (1991);
36. c) Davis F. A., Zhou P., Murphy C. K., Sundarababu G., Qi H., Han W., Przeslawski R. M., Chen B.-C., Carroll P. J., J. Org. Chem., 63, 2273-2280 (1998).