Thionation of ω-hydroxy amides with Lawesson's reagent: Synthesis of thioenamides and sulfur-containing heterocycles

Tetrahedron

Volumn 55, Issue 16, 1999, Pages 5017-5026

  Nishio, Takehiko ^a   Sekiguchi, Hiroshi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Amide Alcohols; Lawesson's Reagent; Sulfur Containing Heterocycles; Thioenamides

Indexed keywords

BENZAMIDE DERIVATIVE; HETEROCYCLIC AMINE; OMEGA HYDROXYAMIDE; PHTHALIDE DERIVATIVE; THIOENAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033574598     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00200-8     Document Type: Article

References (21)

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3. Pederson, B. S.; Lawesson, S.-O. Tetrahedron, 1979, 35, 2433; El-Barbary, A. A.; Clausen, K.; Lawesson, S.-O. Tetrahedron, 1980, 36, 3309; El-Barbary, A. A.; Lawesson, S.-O. Tetrahedron, 1981, 37, 2641; Scheibye, S.; Lawesson, S.-O.; Romming, C. Acta Chem. Scand. B, 1981, 35, 239; Scheibye, S.; Shabana, R.; Lawesson, S.-O. Tetrahedron, 1982, 38, 993; Shabana, R.; Osman, F. H.; Atres, S. S. Tetrahedron, 1994, 50, 6975; Dubau-Assibat, N.; Baceiredo, A.; Bertrand, G. J. Org. Chem., 1995, 60, 3904; Butler, R. N.; MaKenna, E. C.; Grogen, D. Chem. Commun., 1997, 2149.
4. Pederson, B. S.; Lawesson, S.-O. Tetrahedron, 1979, 35, 2433; El-Barbary, A. A.; Clausen, K.; Lawesson, S.-O. Tetrahedron, 1980, 36, 3309; El-Barbary, A. A.; Lawesson, S.-O. Tetrahedron, 1981, 37, 2641; Scheibye, S.; Lawesson, S.-O.; Romming, C. Acta Chem. Scand. B, 1981, 35, 239; Scheibye, S.; Shabana, R.; Lawesson, S.-O. Tetrahedron, 1982, 38, 993; Shabana, R.; Osman, F. H.; Atres, S. S. Tetrahedron, 1994, 50, 6975; Dubau-Assibat, N.; Baceiredo, A.; Bertrand, G. J. Org. Chem., 1995, 60, 3904; Butler, R. N.; MaKenna, E. C.; Grogen, D. Chem. Commun., 1997, 2149.
5. Pederson, B. S.; Lawesson, S.-O. Tetrahedron, 1979, 35, 2433; El-Barbary, A. A.; Clausen, K.; Lawesson, S.-O. Tetrahedron, 1980, 36, 3309; El-Barbary, A. A.; Lawesson, S.-O. Tetrahedron, 1981, 37, 2641; Scheibye, S.; Lawesson, S.-O.; Romming, C. Acta Chem. Scand. B, 1981, 35, 239; Scheibye, S.; Shabana, R.; Lawesson, S.-O. Tetrahedron, 1982, 38, 993; Shabana, R.; Osman, F. H.; Atres, S. S. Tetrahedron, 1994, 50, 6975; Dubau-Assibat, N.; Baceiredo, A.; Bertrand, G. J. Org. Chem., 1995, 60, 3904; Butler, R. N.; MaKenna, E. C.; Grogen, D. Chem. Commun., 1997, 2149.
6. Pederson, B. S.; Lawesson, S.-O. Tetrahedron, 1979, 35, 2433; El-Barbary, A. A.; Clausen, K.; Lawesson, S.-O. Tetrahedron, 1980, 36, 3309; El-Barbary, A. A.; Lawesson, S.-O. Tetrahedron, 1981, 37, 2641; Scheibye, S.; Lawesson, S.-O.; Romming, C. Acta Chem. Scand. B, 1981, 35, 239; Scheibye, S.; Shabana, R.; Lawesson, S.-O. Tetrahedron, 1982, 38, 993; Shabana, R.; Osman, F. H.; Atres, S. S. Tetrahedron, 1994, 50, 6975; Dubau-Assibat, N.; Baceiredo, A.; Bertrand, G. J. Org. Chem., 1995, 60, 3904; Butler, R. N.; MaKenna, E. C.; Grogen, D. Chem. Commun., 1997, 2149.
7. Pederson, B. S.; Lawesson, S.-O. Tetrahedron, 1979, 35, 2433; El-Barbary, A. A.; Clausen, K.; Lawesson, S.-O. Tetrahedron, 1980, 36, 3309; El-Barbary, A. A.; Lawesson, S.-O. Tetrahedron, 1981, 37, 2641; Scheibye, S.; Lawesson, S.-O.; Romming, C. Acta Chem. Scand. B, 1981, 35, 239; Scheibye, S.; Shabana, R.; Lawesson, S.-O. Tetrahedron, 1982, 38, 993; Shabana, R.; Osman, F. H.; Atres, S. S. Tetrahedron, 1994, 50, 6975; Dubau-Assibat, N.; Baceiredo, A.; Bertrand, G. J. Org. Chem., 1995, 60, 3904; Butler, R. N.; MaKenna, E. C.; Grogen, D. Chem. Commun., 1997, 2149.
8. Pederson, B. S.; Lawesson, S.-O. Tetrahedron, 1979, 35, 2433; El-Barbary, A. A.; Clausen, K.; Lawesson, S.-O. Tetrahedron, 1980, 36, 3309; El-Barbary, A. A.; Lawesson, S.-O. Tetrahedron, 1981, 37, 2641; Scheibye, S.; Lawesson, S.-O.; Romming, C. Acta Chem. Scand. B, 1981, 35, 239; Scheibye, S.; Shabana, R.; Lawesson, S.-O. Tetrahedron, 1982, 38, 993; Shabana, R.; Osman, F. H.; Atres, S. S. Tetrahedron, 1994, 50, 6975; Dubau-Assibat, N.; Baceiredo, A.; Bertrand, G. J. Org. Chem., 1995, 60, 3904; Butler, R. N.; MaKenna, E. C.; Grogen, D. Chem. Commun., 1997, 2149.
9. Pederson, B. S.; Lawesson, S.-O. Tetrahedron, 1979, 35, 2433; El-Barbary, A. A.; Clausen, K.; Lawesson, S.-O. Tetrahedron, 1980, 36, 3309; El-Barbary, A. A.; Lawesson, S.-O. Tetrahedron, 1981, 37, 2641; Scheibye, S.; Lawesson, S.-O.; Romming, C. Acta Chem. Scand. B, 1981, 35, 239; Scheibye, S.; Shabana, R.; Lawesson, S.-O. Tetrahedron, 1982, 38, 993; Shabana, R.; Osman, F. H.; Atres, S. S. Tetrahedron, 1994, 50, 6975; Dubau-Assibat, N.; Baceiredo, A.; Bertrand, G. J. Org. Chem., 1995, 60, 3904; Butler, R. N.; MaKenna, E. C.; Grogen, D. Chem. Commun., 1997, 2149.
10. Clausen, K.; Lawesson, S.-O. Bull. Soc. Chim. Belg., 1979, 88, 305; Nouw. J. Chim., 1980, 4, 43; Ishii, A.; Nakayama, J.; Ding, M-X.; Kotaka, N.; Hoshino, M. J. Org. Chem., 1990, 55, 2421; Nugara, P. N.; Huang, N-Z.; Lakshmikanthan, M. V.; Cava, M. P. Heterocycles, 1991, 32, 1559; Ozturk, T. Tetrahedron Lett., 1996, 37, 2821.
11. Clausen, K.; Lawesson, S.-O. Bull. Soc. Chim. Belg., 1979, 88, 305; Nouw. J. Chim., 1980, 4, 43; Ishii, A.; Nakayama, J.; Ding, M-X.; Kotaka, N.; Hoshino, M. J. Org. Chem., 1990, 55, 2421; Nugara, P. N.; Huang, N-Z.; Lakshmikanthan, M. V.; Cava, M. P. Heterocycles, 1991, 32, 1559; Ozturk, T. Tetrahedron Lett., 1996, 37, 2821.
12. Clausen, K.; Lawesson, S.-O. Bull. Soc. Chim. Belg., 1979, 88, 305; Nouw. J. Chim., 1980, 4, 43; Ishii, A.; Nakayama, J.; Ding, M-X.; Kotaka, N.; Hoshino, M. J. Org. Chem., 1990, 55, 2421; Nugara, P. N.; Huang, N-Z.; Lakshmikanthan, M. V.; Cava, M. P. Heterocycles, 1991, 32, 1559; Ozturk, T. Tetrahedron Lett., 1996, 37, 2821.
13. Clausen, K.; Lawesson, S.-O. Bull. Soc. Chim. Belg., 1979, 88, 305; Nouw. J. Chim., 1980, 4, 43; Ishii, A.; Nakayama, J.; Ding, M-X.; Kotaka, N.; Hoshino, M. J. Org. Chem., 1990, 55, 2421; Nugara, P. N.; Huang, N-Z.; Lakshmikanthan, M. V.; Cava, M. P. Heterocycles, 1991, 32, 1559; Ozturk, T. Tetrahedron Lett., 1996, 37, 2821.
14. Clausen, K.; Lawesson, S.-O. Bull. Soc. Chim. Belg., 1979, 88, 305; Nouw. J. Chim., 1980, 4, 43; Ishii, A.; Nakayama, J.; Ding, M-X.; Kotaka, N.; Hoshino, M. J. Org. Chem., 1990, 55, 2421; Nugara, P. N.; Huang, N-Z.; Lakshmikanthan, M. V.; Cava, M. P. Heterocycles, 1991, 32, 1559; Ozturk, T. Tetrahedron Lett., 1996, 37, 2821.
15. Nishio, T. J. Chem. Soc., Chem. Commun., 1989, 205; J. Chem. Soc., Perkin Trans, 1, 1993, 1113.
16. Nishio, T. J. Chem. Soc., Chem. Commun., 1989, 205; J. Chem. Soc., Perkin Trans, 1, 1993, 1113.
17. Nishio, T. J. Org. Chem., 1997, 62, 1106.
18. Part of this was reported in preliminary form; Nishio, T. Tetrahedron Lett., 1995, 36, 6113.
19. Nishio, T. Helv. Chim. Acta, 1998, 81, 1207.
20. In some of these thio-transfer reactions a byproduct was isolated and identified as 2,4,6-tris(p-methoxyphenyl)-1,3,5,2,4,6-trioxatriphosphinane by the comparison of specral data cited in the literature: Wen, T.; Bau, R.; Mackenna, C. E. J. Chem. Soc., Chem. Commun., 1991, 1223.
21. Nishio, T.; Okuda, N.; Mori, Y.; Kashima, C. Synthesis, 1989, 396.