Structure and Additive-free Transamidation of Planar N-Cyano Amides

Although transamidation of amides generally requires metals, additives, or harsh conditions, we present here a facile transamidation of Ncyano amides with various amines at ambient temperature without any additive. N-cyano amides preferred the trans conformation and have a reduced double bond character revealed by crystal analysis. The DFT study indicates that the transamidation reaction proceeds through the direct attack of amine on the amide carbonyl since the LUMO (or LUMO+1) is located at the carbonyl moiety.

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We report a facile transamidation of N-cyano amides with various amines at ambient temperature without any additive. Crystal analysis reveals that N-cyano amides prefer the trans conformation and exhibit reduced double bond character. DFT study suggests that the transamidation reaction proceeds via direct attack of amines on the carbonyl moiety.