Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Behavior of 2-Pyrazolin-5-ones toward Activated Double Bond Systems: Cyanoethylation of 2-Pyrazolin-5-ones
Mohamed Helmi ElnagdiMasaki Ohta
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1973 Volume 46 Issue 12 Pages 3818-3821

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Abstract

3-Methyl-2-pyrazolin-5-one(Ia) reacts with acrylonitrile to yield either 4,4-di(β-cyanoethyl)-5-hydroxy-3-methylpyrazole(IV) or 1,4,4-tri(β-cyanoethyl)-3-methyl-2-pyrazolin-5-one(V) depending on the amount of reagent and the reaction conditions. Ia reacts with ethyl acrylate or crotononitrile to yield the 4-alkylated derivatives VIII and IX respectively. 3-Methyl-l-phenyl-2-pyrazolin-5-one(Ib) reacts with acrylonitrile to yield only 4,4-di(β-cyanoethyl) derivative XII which on hydrolysis affords the corresponding dicarboxylic acid (XIII). 3-Amino-1-phenyl-2-pyrazolin-5-one(Ic) adds to two molecules of ethyl acrylate or acrylonitrile to yield the 4,4-disubstituted derivatives XIV and XV, but only to one molecule of benzalacetophenone to yield the 4-substituted 3-amino-2-pyrazolin-5-one derivative XVIII. The pyrazolopiperidine derivative(XVI) was obtained on treatment of Ic with ethyl crotonate in the presence of sodium ethoxide.

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