Stereoselective synthesis of 4H-5,6-dihydro-1,3-thiazines by the reaction of 3-N-acylamino alcohols with Lawesson's reagent

European Journal of Organic Chemistry

Volumn , Issue 18, 2001, Pages 3553-3557

  Nishio, Takehiko ^a   Konno, Yukako ^a   Ori, Mayuko ^a   Sakamoto, Masami ^b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b Faculty of Engineering   (Japan)

Author keywords

Amino alcohols; Asymmetric synthesis; Sulfur; Sulfur heterocycles

Indexed keywords

4H 5,6 DIHYDRO 1,3 THIAZINE; ALCOHOL DERIVATIVE; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034815058     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200109)2001:18<3553::AID-EJOC3553>3.0.CO;2-U     Document Type: Article

References (36)

1. M. P. Cava, M. I. Levinson, Tetrahedron 1985, 41, 5061-5087;
2. D. Brillon, Sulfur Rep. 1992, 12, 297-338.
3. [2a] B. S. Pedersen, S.-O. Lawesson, Tetrahedron 1979, 35, 2433-2437.
4. [2b] A. A. El- Barbary, K. Clausen, S.-O. Lawesson, Tetrahedron 1980, 36, 3309-3315.
5. [2c] A. A. El-Barbary, S.-O. Lawesson, Tetrahedron 1981, 37, 2641-2646.
6. [2d] S. Sheibye, S.-O. Lawesson, C. Romming, Acta Chem. Scand., Ser. B 1981, 35, 239-246.
7. [2e] S. Sheibye, R. Shabana, S.-O. Lawesson, Tetrahedron 1982, 38, 993-1001.
8. [2f] R. Shabana, F. H. Osman, S. S. Atrees, Tetrahedron 1994, 50, 6975-6988.
9. [2g] N. Dubeu-Assibat, A. Baceiredo, G. Bertrand, J. Org. Chem. 1995, 60, 3904-3906.
10. [2h] R. N. Butler, E. C. MaKenna, D. Grogen, Chem. Commun. 1997, 2149-2150.
11. [2i] Y. A. Ibrahim, A. Z. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, R. A. Palmer, Tetrahedron Lett. 1999, 55, 13457-13462.
12. [3a] K. Clausen, S.-O. Lawesson, Bull. Soc. Chim. Belg. 1979, 88, 305-311.
13. [3b] K. Clausen, S.-O. Lawesson, Nouv. J. Chim. 1980, 4, 43-46.
14. [3c] A. Ishii, J. Nakayama, M.-X. Ding, N. Kataoka, M. Hoshino, J. Org. Chem. 1990, 55, 2421-2427.
15. [3d] P. N. Nugara, N.-Z. Huang, M. V. Lakshmikantham, M. P. Cava, Heterocycles 1991, 32, 1559-1561.
16. [3e] K-T. Kang, J. S. U, Synth. Commun. 1995, 25, 2647-2653.
17. [3f] T. Ozturk, Tetrahedron Lett. 1996, 37, 2821-2824.
18. [3g] C. W. Ong, M. Chen, L. F. Wang, P. C. Shieh, Tetrahedron Lett. 1998, 39, 9191-9192.
19. [3h] E. Ertas, T. Ozturk, Chem. Commun. 2000, 2309-2310
20. T. Nishio, J. Chem. Soc., Chem. Commun. 1989, 205-206;
21. J. Chem. Soc., Perkin Trans. 1 1993, 1113-1117.
22. [5a] T. Nishio, Tetrahedron Lett. 1995, 36, 6113-6116.
23. [5b] T. Nishio, H. Sekiguchi, Tetrahedron 1999, 55, 5017-5026.
24. T. Nishio, J. Org. Chem. 1997, 62, 1106-1111.
25. M. Ori, T. Nishio, Heterocycles (Special issue) 2001, 54, 2011-108.
26. T. Nishio, Helv. Chim. Acta 1998, 81, 1207-1214.
27. M. Ori, T. Nishio, Heterocycles (Special issue) 2000, 52, 111-116.
28. [10a] H. Quiniou, O. Guilloton, in Advances in Heterocyclic Chemistry (Ed.: A. R. Katritzky), Academic Press Inc.: San Diego, California, 1990, Vol. 50; p 85-156.
29. [10b] M. Sainbury, in Comprehensive Heterocyclic Chemistry (Eds.: A. R. Katritzky, C. W. Rees), Pergamon Press, Oxford, 1984; vol. 3; p. 995-1038;
30. M. Sainbury, Comprehensive Heterocyclic Chemistry 1996; vol. 6; p. 383-413 and references cited therein.
31. [10c] N. Yasuda, M. Karikomi, T. Toda, Chem. Lett. 1995, 1141-1142.
32. [10d] A. J. Liepa, S. Saubern, Aust. J. Chem. 1997, 50, 755-758.
33. [10e] P. Wipf, G. B. Hayes, Tetrahedron 1998, 54, 6987-6998.
34. Tables of crystal data are available as supplementary data. Atomic coordinates, bond lengths and angles and thermal parameters of X-ray crystal structures of 5S (CCDC-167043) and 13A (CCDC-167044) have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) +44-1223/ 336-033; Email: deposit@ccdc.cam.ac.uk].
35. D. L. Boger, R. J. Wysocki, Jr, J. Org. Chem. 1989, 54, 714-718;
36. C. Kashima, Y. Yamamoto, Y. Omote, J. Org. Chem. 1975, 40, 526-527.