The reaction of 5-substituted (a=CN, b=COOEt, c=COPh, d=CONH
2) 3, 4-diamino-2-methylthiothiophenes (1a-b) with 1, 3-dicarbonyl compounds (methyl acetoacetate, diethyl or dimethyl acetonedicarboxylate, diketene, ethyl benzoylacetate) gave the corresponding thieno [3, 4-b] [1, 4] diazepine derivatives (4, 5, 8, 9, 11-13). The condensation of 1 with ketenethioacetal derivatives (2-bis (methylthio) methylene-1, 3-indandione, 3, 3-bis (methylthio)-1-(p-substituted phenyl)-2-propen-1-one (a=p-H, b=p-Cl, c=p-Br)) afforded the corresponding diazepine derivatives, 11-substituted 2, 4-bis (methylthio)-3H, 10H-indeno [1', 2' : 7, 6] [1, 4] diazepino [2, 3-c] thiophen-5-ones (15a, b) and 2-cyano-6, 8-bis (methylthio)-4-(p-substituted phenyl)-3H-thieno [3, 4-b] [1, 4] diazepines (19a-c) (a=p-H, b=p-Cl, c=p-Br), in good yields.
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