Abstract

A number of primary thioamides was prepared from the appropriate aliphatic or aromatic nitriles in high yield and then used in syntheses of secondary thioamides. Two reactions between 4-thiothymine derivatives and methylamine were carried out in order to confirm the rearrangement of the H2S molecule in 1-(3-cyanopropyl)-4-thiothymine, leading to an N-methylthioamide (via a primary thioamide intermediate) on further reaction with methylamine. 1-[3-(thiocarbamoyl)propyl]-4-thiothymine gave directly the same product. Evidence for the new hydrogen-bond-promoted reaction is provided. The proposed CSNH…O = C2 bonding scheme seems to be plausible.

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