1,3-Dipolar cycloaddition of nitrile imines with α,β-unsaturated lactones, thiolactones and lactams: Synthesis of ring-fused pyrazoles

Jay Zumbar Chandanshive, Pedro Blas González, William Tiznado, Bianca Flavia Bonini, Julio Caballero, Cristina Femoni, Mauro Comes Franchini

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

1,3-Dipolar cycloaddition of nitrile imines with α,β-unsaturated five- and six-membered lactones, thiolactones and lactams gave ring-fused pyrazoles. Regioisomeric mixtures have been obtained with the 5-substituted pyrazole as the major cycloadduct. Only with the five-membered lactone the major product was the 4-acyl derivative. Computational studies, the use of the topological analysis of the Fukui functions and the potential energy surfaces (PES) theory allowed a theoretical description of the local reactivity in agreement with the observed high regiochemistry and with the role of the heteroatom adjacent to the carbonyl group.

Original languageEnglish
Pages (from-to)3319-3328
Number of pages10
JournalTetrahedron
Volume68
Issue number16
DOIs
Publication statusPublished - 22 Apr 2012

Keywords

  • Dipolar cycloadditions
  • Lactams
  • Nitrile imines
  • Pyrazoles
  • Thiolactones
  • α,β-Unsaturated lactones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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