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Condensation of ethyl phenylpropiolate with some cyanoacetyl and cyanomethylene heterocycles
Author(s) -
AlJallo Hikmat N.,
AlBiaty Ibtisam A.,
AlAzawi Fatin N.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140810
Subject(s) - chemistry , morpholine , phenylhydrazine , hydrate , hydrazine (antidepressant) , pyrrolidine , hydroxylamine hydrochloride , piperidine , organic chemistry , medicinal chemistry , halogenation , alkaline hydrolysis , hydrolysis , chromatography
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.