| Abstract: | N-Cyanoacetyl pyrrolidine, piperidine and morpholine reacted with ethyl phenylpropiolate to give the rearranged Michael addition products III. Some interesting results obtained from the bromination, hydrolysis and reduction of III are reported. 2-Thiophene and 2-furaneaceto-nitriles reacted with ethyl phenylpropiolate to give the Claisen addition products XVIII. Reaction of either III or XVIII with hydrazine hydrate, phenylhydrazine and hydroxylamine hydrochloride afforded 3-phenylpyrazol-5-one, 1,3-diphenylpyrazol-5-one and 3-phenylisoxazol-5-one together with the appropriate starting cyanoacetyl or cyanomethylene compounds, respectively. The mechanism for the formation of the various reaction products beside the ir and nmr spectral results are discussed. |
