Tetrahedron

3-Alkenyl-5-chloropyrazoles: expedient synthesis via heterocyclization of 1, 1-dichloro-4-halo-1-alken-3-ones with hydrazines

GG Levkovskaya, VA Kobelevskaya, EV Rudyakova…

Index: Levkovskaya, Galina G.; Kobelevskaya, Valentina A.; Rudyakova, Elena V.; Ha, Khanh Q.; Samultsev, Dmitrii O.; Rozentsveig, Igor B. Tetrahedron, 2011 , vol. 67, # 10 p. 1844 - 1851

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Citation Number: 12

Abstract

Synthesis of hard-to-reach 5-chloro-3-alkenylpyrazoles was developed via heterocyclization of alkyl-, benzyl-or dialkylhydrazines with 1, 1-dichloro-4-halo-1-alken-3-ones obtained from haloacyl chlorides and vinylidene chloride. The reaction process includes the formation of intermediate 5-chloro-3-(1-haloalkyl) pyrazoles followed by dehydrohalogenation.