インドール誘導体の研究(第6報) : 2-Oxo-4-methylthio-2H-pyrano-[2,3-b]indole 類の合成とその反応

概要

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γ-Methylthio-2-oxindol-3-acrylic acid derivatives (IV) (Table I) were obtained by the reaction of 3-bis(methylthiomethylene)-2-oxindoles (II) and the sodium salts of active methylene compounds. Reaction of IVc with amines gave the corresponding amino derivatives (VI) (Table II), while treatment of IVa, b, c with polyphosphoric acid and their direct fusion afforded 2-oxo-4-methylthiopyrano[2,3-b]indoles (VIII) (Table III). Reaction of VIIIb with amines gave the acid amide derivatives (XII, XIII) (Tables IV and V), while that of VIIIb with the sodium salt of methyl cyanoacetate afforded methyl (1-methyl-β-methylthio-2-oxo-3-indolyl)acrylcyanoacetate (XIV). The reaction of VIIIb, c with sodium cyanide gave indole-2-carbonitrile derivative (XVI) (Table VI), while that of XVIc With amines afforded the corresponding amino derivative (XVIII) (Table VII).
公益社団法人日本薬学会の論文
1967-09-25