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Paper | Regular issue | Vol 57, No. 11, 2002, pp.2045-2064
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9566
Synthesis and Reactivity of (Z)-3-Benzoylamino-4-dimethylamino-2-oxo-3-butene. Preparation of 1-Aryl- and 1-Heteroaryl-substituted 4-Benzoyl-amino-5-methyl-1H-pyrazoles

Urska Bratusek, Simon Recnik, Jurij Svete,* Ljubo Golic, and Branko Stanovnik*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SLO-1000 Ljubljana, Slovenia

Abstract

(Z)-3-Benzoylamino-4-dimethylamino-2-oxo-3-butene (4), prepared from 1-benzoylamino-2-propanone (3) and N,N-dimethylformamide dimethyl acetal, was converted regioselectively by reaction with a series of hydrazines (5) into 1-substituted 4-benzoylamino-5-methyl-1H-pyrazoles (8). Reactions of 4 with primary amines (10) and with dimethylbarbituric acid (12) afforded the dimethylamine substitution products (11) and (13), respectively. Treatment of the butenone (13) with ammonia furnished tetrahydropyrido[2,3—d]pyrimidine derivative (14).