1-(Methyldithiocarbonyl)imidazole: A Reagent of S-Methyldithiocarbonylation

Synlett

Volumn 1997, Issue 11, 1997, Pages 1279-1280

  Sun, Wei Yan ^a,c   Hu, Ji Qing ^b,c   Shi, Yong Ping ^b,c  

^a William Laboratories   (China)

^b Devmt Corp Shanghai Inst O   (China)

^c UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038739587     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1019     Document Type: Article

References (33)

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2. Barton, D.H.R.; Motherwell, W.B. Pure Appl. Chem. 1981, 55, 13. Zard, S.Z. Angew. Chem. Intl. Ed. 1997, 36(7), 673. Jamison, T.F.; Shambayati, S.; Crowe, W.E.; Schreiber, S.L. J. Am. Chem. Soc. 1997, 119, 4353. Hartwig, W. Tetrahedron 1983, 39, 2609. Ramaiah, M. Tetrahedron 1987, 43, 2541.
3. Barton, D.H.R.; Motherwell, W.B. Pure Appl. Chem. 1981, 55, 13. Zard, S.Z. Angew. Chem. Intl. Ed. 1997, 36(7), 673. Jamison, T.F.; Shambayati, S.; Crowe, W.E.; Schreiber, S.L. J. Am. Chem. Soc. 1997, 119, 4353. Hartwig, W. Tetrahedron 1983, 39, 2609. Ramaiah, M. Tetrahedron 1987, 43, 2541.
4. Barton, D.H.R.; Motherwell, W.B. Pure Appl. Chem. 1981, 55, 13. Zard, S.Z. Angew. Chem. Intl. Ed. 1997, 36(7), 673. Jamison, T.F.; Shambayati, S.; Crowe, W.E.; Schreiber, S.L. J. Am. Chem. Soc. 1997, 119, 4353. Hartwig, W. Tetrahedron 1983, 39, 2609. Ramaiah, M. Tetrahedron 1987, 43, 2541.
5. Barton, D.H.R.; Motherwell, W.B. Pure Appl. Chem. 1981, 55, 13. Zard, S.Z. Angew. Chem. Intl. Ed. 1997, 36(7), 673. Jamison, T.F.; Shambayati, S.; Crowe, W.E.; Schreiber, S.L. J. Am. Chem. Soc. 1997, 119, 4353. Hartwig, W. Tetrahedron 1983, 39, 2609. Ramaiah, M. Tetrahedron 1987, 43, 2541.
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13. Harano, K.; Shinohara, I.; Murase, M.; Tisano, T. Heterocycles 1987, 26, 2583. Harano, K.; Shinohara, I.; Sugimoto, S.I.; Matsuok, T.; Tisano, T. Chem. Pharm. Bull. 1989, 37, 576. Harano, K.; Kiyonaga, H.; Sugimoto, S.I.; Matsuok, T.; Tisano, T. Heterocycles 1988, 27, 2327.
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16. Sharma, G.V.M.; Vepachedu, S.R. Tetrahedron Letters 1990, 31(34), 4931. Nicolaou, K.C.; Maligres, P.; Suzuki, T. J. Am. Chem. Soc. 1992, 114, 8890. Barton, D.H.R.; Crich, D.; Motherwell, W.B. Tetrahedron 1985, 41, 3901.
17. Sharma, G.V.M.; Vepachedu, S.R. Tetrahedron Letters 1990, 31(34), 4931. Nicolaou, K.C.; Maligres, P.; Suzuki, T. J. Am. Chem. Soc. 1992, 114, 8890. Barton, D.H.R.; Crich, D.; Motherwell, W.B. Tetrahedron 1985, 41, 3901.
18. Yamamoto K.; Sun, W.Y.; Ohta, M.; Hamada, K.; Deluca, H.F.; Yamada, S. J. Med. Chem. 1996, 39, 2727. Posner G.H. J. Org. Chem. 1997, 62, 3299. Chandhary, A.G.; Rimoldi, J.M.; Kingston, D.G.I. J. Org. Chem. 1993, 58, 3798.
19. Yamamoto K.; Sun, W.Y.; Ohta, M.; Hamada, K.; Deluca, H.F.; Yamada, S. J. Med. Chem. 1996, 39, 2727. Posner G.H. J. Org. Chem. 1997, 62, 3299. Chandhary, A.G.; Rimoldi, J.M.; Kingston, D.G.I. J. Org. Chem. 1993, 58, 3798.
20. Yamamoto K.; Sun, W.Y.; Ohta, M.; Hamada, K.; Deluca, H.F.; Yamada, S. J. Med. Chem. 1996, 39, 2727. Posner G.H. J. Org. Chem. 1997, 62, 3299. Chandhary, A.G.; Rimoldi, J.M.; Kingston, D.G.I. J. Org. Chem. 1993, 58, 3798.
21. Ichikawa, Y. Tetrahedron Letters 1988, 29(39), 4957.
22. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
23. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
24. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
25. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
26. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
27. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
28. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
29. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
30. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
31. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
32. primary alcohols: Cristol, S.J.; Seapy, D.J. J. Org. Chem. 1982, 47, 132. Yamamoto, M.; Uruma, T.; Iwasa, S.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1265. secondary alcohols: Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Chambers, M.S.; Thomas, E.J.; Williams, D.J.; J. Chem. Soc., Chem. Commun. 1987, 1228. Beckwith, A.L.J.; Bowry, V.W.; Schiesser, C.H. Tetrahedron 1991, 47, 615. France, C.J.; McFarlance, I.M.; Newton, C.G.; Pitchen, P. Tetrahedron 1991, 47, 615. Cubero, I.I.; Lopez-Espinosa, M.T.P.; Richardson, A.C.; Asmlid, K.H. Carbohydro. Res. 1993, 242, 281. Ekberg, T.; Magnusson, G. Carbohydro. Res. 1993, 246, 119. tertiary alcohols: Barton, D.H.R.; Parekh, S.I.; Tse, S.L. Tetrahedron Letters 1993, 34(17), 2733. Nicolaou, K.C.; Hwang, C.K.; Smith, A.L. J. Am. Chem. Soc. 1990, 122, 7416. Barton, D.H.R.; Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Letters 1992, 33, 5709.
33. The compound 1 was reported in 1983. See Howes, P.D. and Pianka, M. J. Chem. Soc., Perkin Trans. 1, 1983, 762.