A one-pot, one-operation [3+3] annulation approach to benzothiazines

Angewandte Chemie - International Edition

Volumn 38, Issue 16, 1999, Pages 2419-2421

  Harmata, Michael ^a   Pavri, Neville ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

Aminations annulation; Benzothiazines; Palladium; Sulfoximines

Indexed keywords

BENZOTHIAZINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033549739     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2419::AID-ANIE2419>3.0.CO;2-I     Document Type: Article

References (25)

1. a) M. Harmata, E. O. Schlemper, Tetrahedron Lett. 1987, 28, 5997-6000;
2. b) M. Harmata, Tetrahedron Lett. 1988, 29, 5229-5232;
3. c) M. Harmata, Tetrahedron Lett. 1989, 30, 437-440.
4. a) M. Harmata, R. J. Claassen II, C. L. Barnes, J. Org. Chem. 1991, 56, 5059-5062;
5. b) M. Harmata, R. J. Claassen II, Tetrahedron Lett. 1991, 32, 6497-6500;
6. c) M. Harmata, M. Kahraman, J. Org. Chem. 1998, 63, 6845-6851.
7. a) M. Harmata, B. Herron, Tetrahedron 1991, 47, 8855-8862;
8. b) M. Harmata, M. Kahraman, Synthesis 1994, 142-144;
9. c) M. Harmata, M. Kahraman, Synthesis 1995, 713-716;
10. d) M. Harmata, D. E. Jones, Tetrahedron Lett. 1995, 36, 4769-4772;
11. e) M. Harmata, M. Kahraman, D. E. Jones, N. Pavri, S. E. Weatherwax, Tetrahedron 1998, 54, 9995-10 006.
12. C. R. Johnson, E. U. Jonsson, A. Wambsgans, J. Org. Chem. 1979, 44, 2061-2065.
13. a) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
14. a) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
15. b) J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852-860;
16. c) J. F. Hartwig, Synlett 1997. 329-340;
17. c) J. P. Wolfe, S. Wagaw, J.-F. Marcoux, S. Buchwald, Acc. Chem. Res. 1998, 31, 805-818.
18. C. Bolm, J. P. Hildebrand, Tetrahedron Lett. 1998, 37, 5731-5734.
19. a) C. R. Johnson, R. A. Kirchhoff, G. H. Corkins, J. Org. Chem. 1974, 39, 2458-2459;
20. b) J. Brandt, H.-J. Gais, Tetrahedron: Asymmetry 1997, 8, 909-912.
21. N. Asao, M. Meguro, Y. Yamamoto, Synlett 1994, 185-186.
22. If condensation preceded the formation of the nitrogen-carbon bond it is likely that the stereochemistry of the resulting double bond would be E, thus precluding intramolecular ring formation. On the other hand, one can imagine mechanisms for double-bond isomerization and this mechanistic possibility must be rigorously excluded.
23. A. Jakobs, L. Christiaens, M. Renson, Bull. Soc. Chim. Belg. 1991, 100, 1-4.
24. M. Harmata, C. L. Barnes, Tetrahedron Lett. 1990, 31, 1825-1828.
25. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-116293 (7a), 116515 (9), 116295 (11b), and 116296 (11c). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; email: deposit@ccdc.cam.ac.uk).