Synthesis of 3-benzoyl-4-styryl-2-pyrazolines and their oxidation to the corresponding pyrazoles

Diana C G A Pinto, Artur M S Silva, A. Lévai, José A S Cavaleiro, T. Patonay, José Elguero

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

The 3-benzoyl-4-styryl-2-pyrazolines 2a-g were prepared from the regioselective 1,3-dipolar cycloaddition reactions of (E,E)- cinnamylideneacetophenones 1a-g and diazomethane. The new compounds 3-(2- benzofuranyl)-4-styryl-2-pyrazolines (5c,d) were also obtained as by-products in some cases. The oxidation of the 3-benzoyl-4-styryl-2-pyrazolines 2a-g into 3(5)-benzoyl-4-styrylpyrazoles 3a-g is also reported. Configurational and conformational features of all compounds were established by NMR spectroscopy.

Original languageEnglish
Pages (from-to)2593-2599
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number14
Publication statusPublished - Jul 2000

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Pyrazoles
Diazomethane
Cycloaddition
Cycloaddition Reaction
Nuclear magnetic resonance spectroscopy
Byproducts
Magnetic Resonance Spectroscopy
Oxidation

Keywords

  • (E,E)-Cinnamylideneacetophenones
  • Cycloadditions
  • Nitrogen heterocycles
  • NMR spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of 3-benzoyl-4-styryl-2-pyrazolines and their oxidation to the corresponding pyrazoles. / Pinto, Diana C G A; Silva, Artur M S; Lévai, A.; Cavaleiro, José A S; Patonay, T.; Elguero, José.

In: European Journal of Organic Chemistry, No. 14, 07.2000, p. 2593-2599.

Research output: Contribution to journalArticle

Pinto, Diana C G A ; Silva, Artur M S ; Lévai, A. ; Cavaleiro, José A S ; Patonay, T. ; Elguero, José. / Synthesis of 3-benzoyl-4-styryl-2-pyrazolines and their oxidation to the corresponding pyrazoles. In: European Journal of Organic Chemistry. 2000 ; No. 14. pp. 2593-2599.
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