Journal of Organic Chemistry p. 1090 - 1094 (1982)
Update date:2022-08-05
Topics:
Yokoyama, Masataka
Nakamura, Masaki
Ohteki, Hiroko
Imamoto, Tsuneo
Yamaguchi, Kei-ichi
Condensation of 2-cyano-3-mercapto-3-(methylthio)acrylamide (1) with benzoic acid in the presence of polyphosphate ester gave 5-carbamoyl-4-(methylthio)-2-phenyl-1,3-oxazine-6-thione (6), which, on treatment with boiling ethanol, was easily converted into 5-carbamoyl-4-(methylthio)-2-phenyl-1,3-thiazin-6-one (9).Reduction of 9 with NaBH4 gave its 2,3-dihydro derivative 10.The strucures of 6,9, and 10 were determined by single-crystal X-ray diffraction.A reaction mechanism of this novel S,N double rearrangement is briefly discussed.
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Doi:10.1021/jo00347a027
(1982)Doi:10.1016/0031-9422(89)80021-4
(1989)Doi:10.1139/v77-070
(1977)Doi:10.1016/S0040-4020(01)89928-2
(1987)Doi:10.1248/cpb.29.3124
(1981)Doi:10.1016/S0040-4039(01)82009-8
(1981)
