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The synthesis of some ethyl 3‐(1,2‐dialkylhydrazino)propanoates and their cyclization to 1,2‐dialkyl‐3‐yrazolidinones
Author(s) -
Kornet Milton J.,
Ie Tan Sip
Publication year - 1968
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.5570050315
Subject(s) - chemistry , sodium methoxide , ethyl acrylate , ethyl ester , organic chemistry , medicinal chemistry , ethyl acetate , acrylate , methanol , polymer , monomer
The preparation of several ethyl 3‐(1,2‐dialkylhydrazino)propanoates (III) by the reaction of 1,2‐dialkylhydrazines with acrylates is described. Compound III is accompanied by small amounts of the bis addition products (V) in the reactions of ethyl acrylate with a few of the hydrazines. Cyclization of III to 1,2‐dialkyl‐3‐pyrazolidinones (IV) was achieved with sodium methoxide. 1,2‐Dialkyl‐5‐methyl‐3‐pyrazolidinones were obtained directly from 1,2‐dialkylhydrazines and ethyl crotonate. A procedure for the preparation of 1,2‐di‐(2‐ethoxycarbonylethyl)hydrazines is also given.