The Three-Component Biginelli Reaction: A Combined Experimental and Theoretical Mechanistic Investigation

被引：114

作者：

De Souza, Rodrigo O. M. A. ^{[1
]}

da Penha, Eduardo T. ^{[1
]}

Milagre, Humberto M. S. ^{[2
]}

Garden, Simon J. ^{[1
]}

Esteves, Pierre M. ^{[1
]}

Eberlin, Marcos N. ^{[3
]}

Antunes, Octavio A. C. ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, Inst Chem, BR-21941909 Rio De Janeiro, Brazil

[2] Sao Poulo State Univ, Dept Biochem & Microbiol, BR-13506900 Rio Claro, SP, Brazil

[3] Univ Estadual Campinas, Inst Chem, ThoMSon Mass Spectrometry Lab, BR-13084971 Campinas, SP, Brazil

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 38期

基金：

巴西圣保罗研究基金会;

关键词：

Biginelli reaction; density functional calculations; electrospray mass spectrometry; heterocyclic compounds; reaction mechanisms; ELECTROSPRAY-IONIZATION MASS; ONE-POT SYNTHESIS; SOLVENT-FREE CONDITIONS; DIELS-ALDER REACTIONS; SOLID-PHASE; CONDENSATION REACTION; DIHYDROPYRIMIDINE SYNTHESIS; EFFICIENT SYNTHESIS; PARALLEL SYNTHESIS; ORGANIC-SYNTHESIS;

D O I：

10.1002/chem.200900470

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：9799 / 9804

页数：6

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