Sulfur-containing heterocycles derived by reaction of N-thioacylamino alcohols with Lawesson's reagent and saponification of N-thioacylamino esters

Heterocycles

Volumn 58, Issue , 2002, Pages 203-212

  Nishio, Takehiko ^a   Sekiguchi, Hiroshi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BENZOXAZINE DERIVATIVE; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; LAWESSON REAGENT; POTASSIUM CARBONATE; REAGENT; SULFUR DERIVATIVE; THIAZINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; ELIMINATION REACTION; REACTION ANALYSIS; SAPONIFICATION;

EID: 0037159698     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-02-S(M)9     Document Type: Article

References (38)

1. th edn", Vol. E8b, ed. by E. Schumann, Thieme, Stuttgart, 1994, pp. 1; M. Sainsbury, 'Comprehensive Heterocyclic Chemistry II', Vol. 6, eds. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon Press, Oxford, 1996, pp. 301 and pp. 383.
2. th edn", Vol. E8b, ed. by E. Schumann, Thieme, Stuttgart, 1994, pp. 1; M. Sainsbury, 'Comprehensive Heterocyclic Chemistry II', Vol. 6, eds. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon Press, Oxford, 1996, pp. 301 and pp. 383.
3. th Edn.", Vol. E8b, ed. by E. Schumann, Thieme, Stuttgart, 1994, pp. 1; M. Sainsbury, 'Comprehensive Heterocyclic Chemistry II', Vol. 6, eds. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon Press, Oxford, 1996, pp. 301 and pp. 383.
4. th edn", Vol. E8b, ed. by E. Schumann, Thieme, Stuttgart, 1994, pp. 1; M. Sainsbury, 'Comprehensive Heterocyclic Chemistry II', Vol. 6, eds. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon Press, Oxford, 1996, pp. 301 and pp. 383.
5. M. P. Cava and M. L. Levinson, Tetrahedron, 1985, 41, 5061; R. A. Cherkasov, G. A. Kutyrev, and A. N. Pudovik, Tetrahedron, 1985, 41, 2567; D. Brillon, Sulfur Rep., 1992, 12, 297.
6. M. P. Cava and M. L. Levinson, Tetrahedron, 1985, 41, 5061; R. A. Cherkasov, G. A. Kutyrev, and A. N. Pudovik, Tetrahedron, 1985, 41, 2567; D. Brillon, Sulfur Rep., 1992, 12, 297.
7. M. P. Cava and M. L. Levinson, Tetrahedron, 1985, 41, 5061; R. A. Cherkasov, G. A. Kutyrev, and A. N. Pudovik, Tetrahedron, 1985, 41, 2567; D. Brillon, Sulfur Rep., 1992, 12, 297.
8. (a) K. Clausen and S.-O. Lawesson, Bull. Soc. Chim. Belg., 1979, 88, 305;
9. (b) K. Clausen and S.-O. Lawesson, Nouv. J. Chim., 1980, 4, 43;
10. (c) A. Ishii, J. Nakayama, M.-X. Ding, N. Kotaka, and M. Hoshino, J. Org. Chem., 1990, 55, 2421; J. Nakayama, H. Motoyama, H. Machida, M. Shimomura, and M. Hoshino, Heterocycles, 1984, 22, 1527; A Ishii, T. Omata, K. Umezawa, and J. Nakayama, Bull. Chem. Soc. Jpn, 2000, 73, 729;
11. (c) A. Ishii, J. Nakayama, M.-X. Ding, N. Kotaka, and M. Hoshino, J. Org. Chem., 1990, 55, 2421; J. Nakayama, H. Motoyama, H. Machida, M. Shimomura, and M. Hoshino, Heterocycles, 1984, 22, 1527; A Ishii, T. Omata, K. Umezawa, and J. Nakayama, Bull. Chem. Soc. Jpn, 2000, 73, 729;
12. (c) A. Ishii, J. Nakayama, M.-X. Ding, N. Kotaka, and M. Hoshino, J. Org. Chem., 1990, 55, 2421; J. Nakayama, H. Motoyama, H. Machida, M. Shimomura, and M. Hoshino, Heterocycles, 1984, 22, 1527; A Ishii, T. Omata, K. Umezawa, and J. Nakayama, Bull. Chem. Soc. Jpn, 2000, 73, 729;
13. (d) P. N. Nugara, N.-Z. Huang, M. V. Lakshmikanthan, and M. P. Cava, Heterocycles, 1991, 32, 1559;
14. (e) T. Nishio, Tetrahedron Lett., 1995, 36, 6113; T. Nishio and H. Sekiguchi, Tetrahedron, 1999, 55, 5017;
15. (e) T. Nishio, Tetrahedron Lett., 1995, 36, 6113; T. Nishio and H. Sekiguchi, Tetrahedron, 1999, 55, 5017;
16. (f) K. Kang and J. S. U, Synth. Commun., 1995, 25, 2647;
17. (g) T. Ozturk, Tetrahedron Lett., 1996, 37, 2821;
18. (h) C. W. Ong, C. M. Chen, L. F. Wang, and P. C. Shieh, Tetrahedron Lett., 1998, 39, 9191;
19. (i) T. Nishio, J. Org. Chem., 1997, 62, 1106;
20. (j) T. Nishio, Helv. Chim. Acta, 1998, 81, 1207;
21. (k) M. Ori and T. Nishio, Heterocycles, 2000, 52, 111;
22. (l) M. Ori and T. Nishio, Heterocycles, 2001, 54, 201;
23. (m) T. Nishio, Y. Konno, M. Ori, and M. Sakamoto, Eur. J. Org. Chem., 2001, 3553;
24. (n) T. Nishio and M. Ori, Helv. Chim. Acta, 2001, 84, 2347;
25. (o) A. A. Kiryanov, P. Sampson, and A. J. Seed, J. Org. Chem., 2001, 66, 7925.
26. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
27. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
28. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
29. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
30. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
31. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
32. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
33. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
34. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
35. B. S. Pederson and S.-O. Lawesson, Tetrahedron, 1979, 35, 2433; A. A. El-Barbary, K. Clausen, and S.-O. Lawesson, Tetrahedron, 1980, 36, 3309; A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 1981, 37, 2641; S. Sheibye, S.-O. Lawesson, and C. Romming, Acta Chem. Scand. B, 1981, 35, 239; S. Sheibye, R. Shabana, and S.-O. Lawesson, Tetrahedron, 1982, 38, 993; R. Shabana, F. Osman, and S. S. Atres, Tetrahedron, 1994, 50, 6975; N. Duban-Assibat, A. Baceiredo, and G. Betrand, J. Org. Chem., 1995, 60, 3904; R. N. Butler, E. C. Makenna, and D. Grogen, Chem. Commun., 1997, 2149; Y. A. Ibrahim, A. M. Kadry, M. R. Ibrahim, J. N. Lisgarten, B. S. Potter, and R. A. Palmer, Tetrahedron, 1999, 55, 13457; S-L. Deng and D-Z. Liu, Synthesis, 2001, 2445.
36. T. Nishio, J. Chem. Soc., Chem. Commun., 1989, 205; J. Chem. Soc., Perkin Trans. 1, 1993, 1113.
37. T. Nishio, J. Chem. Soc., Chem. Commun., 1989, 205; J. Chem. Soc., Perkin Trans. 1, 1993, 1113.
38. P. Lafargue, P. Guenol, and J-P. Lellouche, Synlett, 1995, 171.