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

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

29 Citas (Scopus)

Resumen

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.

Idioma originalInglés
Páginas (desde-hasta)3319-3328
Número de páginas10
PublicaciónTetrahedron
Volumen68
N.º16
DOI
EstadoPublicada - 22 abr 2012

Áreas temáticas de ASJC Scopus

  • Bioquímica
  • Descubrimiento de medicamentos
  • Química orgánica

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