1,3-dipolar cycloaddition of nitrile imines with cyclic α-β-unsaturated ketones: A regiochemical route to ring-fused pyrazoles

Jay Zumbar Chandanshive, Bianca Flavia Bonini, William Tiznado, Carlos A. Escobar, Julio Caballero, Cristina Femoni, Mariafrancesca Fochi, Mauro Comes Franchini

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

1,3-Dipolar cycloadditions of C-carboxymethyl-N-arylnitrile imines with cyclic α,β-unsaturated ketones of various sizes have been studied. After cycloaddition, oxidative aromatization gives the ring-fused pyrazoles. Computational studies and the use of topological analyses of the Fukui functions allows a theoretical description of the local reactivity that is in agreement with the experimentally observed regiochemistry.

Original languageEnglish
Pages (from-to)4806-4813
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number25
DOIs
Publication statusPublished - Sep 2011

Keywords

  • Computational chemistry
  • Cycloaddition
  • Fused-ring systems
  • Ketones
  • Nitrile imines

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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