Reaction of 6-Aminouracils with Ketenethioacetals

概要

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Reaction of ketenethioacetals [methyl 2-cyano-3,3-bis (methylthio) acrylate (2), 3,3-bis-(methylthio)-2-phenylsulfonylacrylonitrile (13)] with 6-aminouracils (1a : R^1=R^2=Me, 1b : R^1=Ph, R^2=H) in the presence of potassium carbonate followed by cyclization under reflux in diphenyl ether gave the corresponding 5-amino-6-methoxycarbonyl-7-methylthiopyrido [2,3-d]-pyrimidine-2,4 (1H, 3H)-dione derivatives (4a, b). Reaction of other ketenethioacetals [2-cyano-3,3-bis (methylthio) acrylonitrile (10), dimethyl bis (methylthio) methylenemalonate (18), α-oxo ketenethioacetals (21a-e)] with 1 directly afforded pyrido [2,3-d] pyrimidine derivatives (11a, b, 20a, b, 23a-e) in good yields. 5-Amino-7-methylthiopyrimido [4,5-d] pyrimidine-2,4 (1H, 3H)-dione derivatives (16a-c) were also synthesized from 6-aminouracils (1a, b) and dimethyl cyanoimidodithiocarbonate (15) in a manner similar to that used for the preparation of compound 11a.
社団法人日本薬学会の論文
1984-01-25