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Metal-free Michael addition-initiated three-component reaction for the regioselective synthesis of highly functionalized pyridines: scope, mechanistic investigations and applications

Christophe Allais 1 Frédéric Liéby-Müller 1 Jean Rodriguez 1 Thierry Constantieux 1 
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : A metal-free and completely regioselective three-component synthesis of highly functionalized pyridines from 1,3-dicarbonyl derivatives and Michael acceptors has been achieved. Activated Michael acceptors, that is, β,γ-unsaturated α-oxo carbonyl derivatives, were utilized, allowing substitution at the 4-position and remarkable functional diversity at the 2-position of the pyridine ring. The scope and limitations of this environmentally friendly domino reaction are disclosed, with full experimental data, and the results of mechanistic investigations are discussed.
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https://hal.archives-ouvertes.fr/hal-00861780
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Submitted on : Friday, September 13, 2013 - 2:38:54 PM
Last modification on : Tuesday, December 14, 2021 - 8:36:12 AM

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Christophe Allais, Frédéric Liéby-Müller, Jean Rodriguez, Thierry Constantieux. Metal-free Michael addition-initiated three-component reaction for the regioselective synthesis of highly functionalized pyridines: scope, mechanistic investigations and applications. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2013, pp.4131-4145. ⟨10.1002/ejoc.201300246⟩. ⟨hal-00861780⟩

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