Sulfonyl Ketenethioacetal(第4報)N-Bis(methylthio)methylene-p-tolysulfonamideを利用するIsoquinoline誘導体の合成

概要

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Treatment of methyl 2-(1-cyano-2-methylthio-2-p-tolylsulfonylaminoethenyl) benzoate (III), prepared from N-bis (methylthio) methylene-p-tolylsulfonamide (Ia) and o-methoxycarbonylphenylacetonitrile (II) in the presence of sodium hydride with hydrochloric acid, yielded 4-cyano-1,2-dihydro-3-methylthioisoquinolin-1-one (V). Similarly, the reaction of II with N-bis (methylthio) methylenecyanamide (Ib) afforded a good yield of 2,4-dicyano-1,2-dihydro-3-methylthioisoquinolin-1-one (IV). Compound III reacted with ethanolamine, benzylamine, and hydrazine hydrate to give the corresponding 3-amino-4-cyano-1,2-dihydroisoquinolin-1-ones (VIIa, b) and 1-amino-4,5-dihydro-p-tolysulfonylpyrazolo [3,4-c] isoquinolin-5-one (VIII). The reaction of III with o-phenyl-enediamine and ethylenediamine gave good yields of the corresponding benzimidazo [2,1-b] isoquinolin-7-one (IX) and imidazo [1,2-b] isoquinolin-5 (5H)-one (X).
社団法人日本薬学会の論文
1980-04-25