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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 11, pp 1687–1690 | Cite as

Synthesis and Acylation of 3-Aryl-5-(2-phenylethynyl)-4,5-dihydro-1H-pyrazoles

  • I. S. Odin
  • A. A. GolovanovEmail author
  • V. V. Bekin
  • V. S. Pisareva
LETTERS TO THE EDITOR

The polycentric character of vinylacetylenyl ketones significantly affects the reactions of these compounds with hydrazines. For instance, the triple bond of (E)-1,5-diphenylpent-1-ene-4-yn-3-one (1) reacts with acetylhydrazine, forming 1-(5-hydroxy-3-phenyl-5-styryl-4,5-dihydro-1Н-pyrazol-1-yl)ethanone [1], while the double bond reacts with phenylhydrazine, resulting in 1,5-diphenyl-3-phenylethynyl-4,5-dihydro-1Н-pyrazole [2]. Both of the multiple bonds in the ketone 1 react with hydrazine hydrate, producing a mixture of 3-(1-hydrazi-nyl-2-phenylethyl)-5-phenyl-1Н-pyrazole and 3-(2-hydrazinyl-2-phenylethyl)-5-phenyl-1Н-pyrazole [3].

Cyclization reactions leading to disubstituted furans [ 4, 5, 6] and acetylenylaziridines [ 7] are known for the arylacetylenylvinyl ketones 2, which are structural isomers of the vinylacetylenyl ketones 1. According to published data [ 8], such ketones are of interest also for the synthesis of potentially biologically active pyrazolines, although no other...

Keywords

hydrazine hydrate pyrazolines vinylacetylene ketones N-acylation cyclization 

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • I. S. Odin
    • 1
  • A. A. Golovanov
    • 1
    Email author
  • V. V. Bekin
    • 1
  • V. S. Pisareva
    • 1
  1. 1.Togliatti State UniversityTogliattiRussia

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