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Please use this identifier to cite or link to this item: http://dspace.utalca.cl/handle/1950/9095

Title: 1,3-Dipolar cycloaddition of nitrile imines with alpha,beta-unsaturated lactones, thiolactones and lactams: synthesis of ring-fused pyrazoles
Authors: Chandanshive, J.Z.
Gonzalez, P.B.
Tiznado, W.
Bonini, B.F. .
Caballero, J.
Femoni, C.
Franchini, M.C.
Keywords: Dipolar cycloadditions
Nitrile imines
Pyrazoles
alpha,beta-Unsaturated lactones
Thiolactones
Lactams
Issue Date: Apr-2012
Publisher: PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Citation: TETRAHEDRON Volume: 68 Issue: 16 Pages: 3319-3328 DOI: 10.1016/j.tet.2012.02.068
Abstract: 1,3-Dipolar cycloaddition of nitrile imines with alpha,beta-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. (C) 2012 Elsevier Ltd. All rights reserved.
Description: Caballero, J (Caballero, Julio). Univ Talca, Fac Ingn Bioinformat, Ctr Bioinformat & Simulac Mol, Casilla 721, Talca, Chile
URI: http://dspace.utalca.cl/handle/1950/9095
ISSN: 0040-4020
Appears in Collections:Artículos en publicaciones ISI - Universidad de Talca

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