A. Oku, S. Nakaoji, T. Kadono
Oct 1, 1979
Citations
0
Influential Citations
11
Citations
Journal
Bulletin of the Chemical Society of Japan
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.