Acyl Cyanide. V. The Synthesis of 1-Cyano-1-alkenyl Esters by the Reaction of Acyl Cyanides with Acid Anhydrides and Isocyanates

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Abstract
The reactions of enolizable acyl cyanides (acetyl, propionyl, and isobutyryl cyanide) with acid anhydrides (acetic, propionic, butyric, isobutyric, and benzoic anhydride) in the presence of a catalytic amount of tertiary amines (pyridine, lutidines, 4-(dimethylamino)pyridine) produced the corresponding 1-cyano-1-alkenyl carboxylates. In the reactions of propionyl cyanide, (Z)-1-cyano-1-propenyl carboxylates were formed predominantly over the (E)-isomers (isomer ratios Z⁄E were ca. 80/20). The reactions of the cyanides with isocyanates also gave the corresponding 1-cyano-1-alkenyl carbamates in moderate yields, and the acid-treatments of 1-cyano-2-methyl-1-propenyl phenylcarbamate induced its annelation into 3-phenyl-1,3-oxazolidine-2,4-dione derivatives.