Sulfonyl Ketenethioacetal(第5報)2,3-Dihydro-2-bis(methylthio)methylene-3-oxobenzo[b]thiophene 1,1-Dioxideの合成と反応

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Sulfonyl ketenethioacetal, 2,3-dihydro-2-bis (methylthio) methylene-3-oxobenzo [b] thiophene 1,1-dioxide (3), was obtained by the reaction of 2,3-dihydro-3-oxobenzo [b] thiophene 1,1-dioxide (1) with carbon disulfide in the presence of sodium hydroxide in dimethyl sulfoxide, followed by treatment with methyl iodide. The reaction of 3 with various amines gave the corresponding amine derivatives and heterocyclic compounds (imidazoline, hexahydropyrimidine, oxazoline, benzimidazoline, quinazoline, and thiazoline). The reaction of 3 with active methylene compounds gave the displacement products (12a-c) of a methylthio group and the heterocyclic compounds, benzothieno [3,2-b] pyridine derivatives (13a-c), in good yields. Similarly, the reaction of 3 with enamines afforded a good yield of corresponding compounds (17 and 18). The reaction of 3 with sodium cyanide in dimethyl sulfoxide gave 2-(1-cyano-1-methylthio) methylene-2,3-dihydro-3-oxobenzo [b] thiophene 1,1-dioxide (19) in good yield. The reaction of 19 with aniline or N, N-dimethylaniline also gave the corresponding displacement products (20 and 21) of methylthio group in good yields.
社団法人日本薬学会の論文
1984-02-25