Abstract
Aliphatic α-(acylamino)nitriles react with formic acid at room temperature to give the corresponding α-(acylamino) carboxamides with concomitant formation of one mole of carbon monoxide. This new reaction, which was first observed with 2-acylamino-2-cyano-3,6-dihydro-2H-thiapyranes 1, can also be used to convert other N-(α-cyanoalkyl) amides such as N-cyanomethylbenzamides 3, 5 and the 3,4-dihydro Reissert compound 16 into the corresponding carboxamides. Another application is a synthesis of 2-formylaminoacetamides 11. A mechanism for the reaction is proposed.
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