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Reaction of hydrazonyl chlorides and carboalkoxymethylene triphenylphosphoranes to give 5‐alkoxy substituted pyrazoles
Author(s) -
Padwa Albert,
MacDonald J. Gavin
Publication year - 1987
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.5570240457
Subject(s) - chemistry , hydrazone , alkoxy group , nitrile , reagent , imine , medicinal chemistry , wittig reaction , chloride , organic chemistry , catalysis , alkyl
The reaction of ethyl chloroglyoxylate phenyl hydrazone and diphenyl hydrazonyl chloride with several carboalkoxymethylene triphenylphosphoranes has been examined. The products isolated correspond to N ‐phenyl‐3‐carboalkoxy‐5‐alkoxy substituted pyrazoles. The mechanism advanced to account for the formation of the products involves the stepwise addition of a nitrile imine intermediate with the Wittig reagent.