The chemistry of cyanoacetylenes. Part II. Cyanoenamines, their preparation and reactions

Abstract

Cyanoenamines were prepared by addition of cyclic secondary amines to cyanoacetylene. Acidic hydrolysis of 3-morpholinoacrylonitrile afforded formylacetic acid. Treatment of the same cyanoenamine with acyl chlorides gave, unexpectedly, 4-morpholinobutadiene-1,3-dicarbonitrile. Reactions of 3-aziridin-1-ylacrylonitrile with p-nitrobenzoic acid, sodium iodide in acetone, and sodium iodide in carbon disulphide afforded 2-(2-cyanovinyl-amino)ethyl p-nitrobenzoate, 3-(2,2-dimethyl-1,3-oxazolidin-1-yl)acrylonitrile, and 3-(2-thioxo-1,3-thiazolidin-1-yl)acrylonitrile, respectively.