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Type: Artigo de periódico
Title: The Three-Component Biginelli Reaction: A Combined Experimental and Theoretical Mechanistic Investigation
Author: De Souza, ROMA
da Penha, ET
Milagre, HMS
Garden, SJ
Esteves, PM
Eberlin, MN
Antunes, OAC
Abstract: Biginelli reactions have been monitored by direct infusion electrospray ionization mass spectrometry (ESI-MS) and key cationic intermediates involved in this three-component reaction have been intercepted and further characterized by tandem MS experiments (ESI-MS/MS). Density functional theory calculations were also used to investigate the feasibility of the major competing mechanisms proposed for the Biginelli reaction. The experimental and theoretical results were found to corroborate the iminium mechanism proposed by Folkers and Johnson, whereas no intermediates directly associated with either the more energy demanding Knoevenagel or enamine mechanisms could be intercepted.
Subject: Biginelli reaction
density functional calculations
electrospray mass spectrometry
heterocyclic compounds
reaction mechanisms
Country: Alemanha
Editor: Wiley-v C H Verlag Gmbh
Citation: Chemistry-a European Journal. Wiley-v C H Verlag Gmbh, v. 15, n. 38, n. 9799, n. 9804, 2009.
Rights: fechado
Identifier DOI: 10.1002/chem.200900470
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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