1,3-Dipolar cycloaddition of nitrile imines with alpha,beta-unsaturated lactones, thiolactones and lactams: synthesis of ring-fused pyrazoles

dc.creatorChandanshive, J.Z.
dc.creatorGonzalez, P.B.
dc.creatorTiznado, W.
dc.creatorBonini, B.F. .
dc.creatorCaballero, J.
dc.creatorFemoni, C.
dc.creatorFranchini, M.C.
dc.date2012-11-28T21:14:42Z
dc.date2012-11-28T21:14:42Z
dc.date2012-04
dc.date.accessioned2017-03-07T14:59:00Z
dc.date.available2017-03-07T14:59:00Z
dc.identifierTETRAHEDRON Volume: 68 Issue: 16 Pages: 3319-3328 DOI: 10.1016/j.tet.2012.02.068
dc.identifier0040-4020
dc.identifierhttp://dspace.utalca.cl/handle/1950/9095
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/375991
dc.descriptionCaballero, J (Caballero, Julio). Univ Talca, Fac Ingn Bioinformat, Ctr Bioinformat & Simulac Mol, Casilla 721, Talca, Chile
dc.description1,3-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.
dc.languageen
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
dc.subjectDipolar cycloadditions
dc.subjectNitrile imines
dc.subjectPyrazoles
dc.subjectalpha,beta-Unsaturated lactones
dc.subjectThiolactones
dc.subjectLactams
dc.title1,3-Dipolar cycloaddition of nitrile imines with alpha,beta-unsaturated lactones, thiolactones and lactams: synthesis of ring-fused pyrazoles
dc.typeArtículos de revistas


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