A New and Convenient Access to N-Alkoxypyridine-2(1H)-thiones

Synlett

Volumn 1996, Issue 12, 1996, Pages 1206-1208

  Hartung, Jens ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542709243     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5705     Document Type: Article

References (31)

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6. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
7. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
8. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
9. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
10. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
11. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
12. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
13. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
14. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
15. Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230. For recent work on alkoxyl radicals see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095; Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett., 1994, 35, 2049; Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett, 1994, 35, 1003; Lee, E.; Lee, C.; Tae, J.S.; Whang, H.S., Li, K.S. Tetrahedron Lett., 1993, 34, 2343-2346; Banks, J.T.; Scaiano, J.C. J. Am. Chem. Soc., 1993, 115, 6409; Goosen, A.; McCleland, C.W.; Rinaldi, F.C. J. Chem. Soc., Perkin Trans. 2, 1993, 279; Avila, D.A.; Lusztyk, J.; Ingold, K.U. J. Am. Chem. Soc., 1992, 114, 6576; Newcomb, M.; Kumar, M.U.; Boivin, J.; Crépon, E.; Zard, S.Z. Tetrahedron Lett., 1991, 32, 45; Johns, A.; Murphy, J.A. Tetrahedron Lett., 1988, 29, 837.
16. Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706.
17. Hartung, J.; Hiller, M.; Schmidt, P. Liebigs Ann. 1996, 1425.
18. Hartung, J.; Hiller, M.; Schmidt, P. Chem. Eur. J. 1996, 2, 1014.
19. Barton, D.H.R.; Samadi, M. Tetrahedron 1992, 48, 7083; Barton, D.H.R.; Chen, C.; Wall, G.M. Tetrahedron 1991, 47, 6127.
20. Barton, D.H.R.; Samadi, M. Tetrahedron 1992, 48, 7083; Barton, D.H.R.; Chen, C.; Wall, G.M. Tetrahedron 1991, 47, 6127.
21. 3 both 1.1-fold in excess over the alcohol 7 affords the highest yields in pyridinethiones 8.
22. 2, MTB).
23. 23NOS (313.5): calcd. C 72.80, H 7.40, N 4.47, S 10.23; found C 72.57, H 7.54, N 4.45, S 10.00.
24. Elimination, e.g. the formation of styrene from α-phenylethanol 7e, does not seem to be a problem in this reaction.
25. 2 was generally higher than at 25°C or at 0°C. The yields of 8 drop if THF is used as the solvent and no pyridinethiones 8 are obtained in DMF.
26. Jones, R.A.; Katritzky, A.R. J. Chem. Soc. 1958, 3610; Phillips, M.A.; Shapiro, H. J. Chem. Soc. 1942, 584.
27. Jones, R.A.; Katritzky, A.R. J. Chem. Soc. 1958, 3610; Phillips, M.A.; Shapiro, H. J. Chem. Soc. 1942, 584.
28. 2, MTB).
29. 3 in the absence of an alcohol 7 affords 2(1H)-pyridinethione (10) in 80-85% yield.
30. For a cleavage of disulfide bonds by triphenylphosphine in closely related reactions see: Ueki, M.; Maruyama, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1971, 44, 1108; Barton, D.H.R.; Motherwell, W.B.; Simon, E.S.; Zard, S.Z. J. Chem. Soc., Perkin Trans. 1 1986, 2243.
31. For a cleavage of disulfide bonds by triphenylphosphine in closely related reactions see: Ueki, M.; Maruyama, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1971, 44, 1108; Barton, D.H.R.; Motherwell, W.B.; Simon, E.S.; Zard, S.Z. J. Chem. Soc., Perkin Trans. 1 1986, 2243.