インドール誘導体の研究(第11報) : 3-Indolylacetonitrile誘導体と二硫化炭素との反応

概要

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In the reaction of 3-indoleacetonitrile derivatives and carbon disulfide, indole derivatives without a substituent in 2-position afford ketenethioacetal derivatives (II) while those with carbonyl or carboxyl in 2-position form condensed thiopyrone ring, thiopyrano-[3,4-b] indole derivatives (III). Substitution of the methylthio group in these II and III compounds with amines was carried out. In the reaction of III and hydrazine hydrate, the product was a ring-cleaved 2-(2-hydrazinocarbonyl-3-indolyl)-3-hydrazino-3-mercaptoacrylonitrile (IX) whose treatment with ketone or aldehyde afforded a cyclized product, 4-cyano-3-mercaptopyrido [3,4-b] indole derivative. Treatment of IX with carbon disulfide and dimethyl sulfate resulted in the formation of a compound with a thiadiazole ring, 5-cyano-3-methylthio-1-oxo-1,3,4-thiadiazolo [2,3-b] harman (XV).
公益社団法人日本薬学会の論文
1971-02-25