複素環Ketenethioacetal誘導体の研究(第2報)1,4-Dioxo-1,2,3,4-tetrahydroisoquinolineと二硫化炭素との反応

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Application of carbon disulfide and dimethyl sulfate to 1,4-dioxo-1,2,3,4-tetrahydro-isoquinoline (I) in ammonia water gave methyl 1,4-dioxo-1,2,3,4-tetrahydroisoquinoline-3-dithiocarboxylate (II) which was further methylated with methyl iodide to 3-bis(methylthio)methylene-1,4-dioxo-1,2,3,4-tetrahydroisoquinoline (III). Application of alkyl bromoacetate to II, in the presence of potassium carbonate gave 1-alkoxycarbonyl-3-alkoxy-carbonylmethylthio-5-oxo-4H, 5H-thieno[3,4-c]isoquinolines (IXa, b). II was also derived to dimethyl 6,11-dioxo-1-methylthio-3,4,6,11-tetrahydro[1,4]thiazino[4,3-b]isoquinoline-3,4-dicarboxylate (X) by the action of dimethyl acetylenedicarboxylate. Treatment of II or III with phosphorus pentasulfide gave 3,3,4,5-tetrahydro-1,2-dithiolo[4,3-c]isoquinoline-3,5-dithione (XI), which the reaction of III with various amines afforded the corresponding amino derivatives (XIII, XIV, and XV). The reaction of III and sodium cyanide gave 3-cyano(methylthio)methylene-1,4-dioxo-1,2,3,4-tetrahydroisoquinoline (XVII) which reacted with hydrazine hydrate to from 3,6-dioxo-4-methylthio-2,3,5,6-tetrahydropyri- dazino[4,3-c]isoquinoline (XVIII).
社団法人日本薬学会の論文
1974-05-25