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Reactions of acetylenic β‐keto cyanides and β‐keto esters with different ammonia derivatives
Author(s) -
AlJallo H.,
Shandala M.,
AlHajjar F.,
AlJabour N.
Publication year - 1976
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.5570130307
Subject(s) - chemistry , semicarbazide , phenylhydrazine , hydrazine (antidepressant) , ammonia , hydroxylamine , hydrochloride , hydrate , hydroxylamine hydrochloride , organic chemistry , medicinal chemistry , alcohol , ketone , methylamine , derivative (finance) , chromatography , financial economics , economics
Different aryl substituted acetylenic β‐keto cyanides (IAa‐o) and β‐keto esters (IBa‐o) reacted with each of hydrazine hydrate, phenylhydrazine, hydroxylamine hydrochloride and semicarbazide hydrochloride in boiling alcohol to give the same heterocyclic nucleus for each type of ammonia derivative. In certain cases, intermediate acetylenic hydrazides were isolated at room or zero temperatures and cyclized to give the appropriate pyrazol‐5‐one compounds when healed above their melting points. It is concluded that Michael addition is favoured at elevated temperatures and Claisen addition is favoured at lower temperatures.