1206900-98-2Relevant academic research and scientific papers
Metal-free michael-addition-initiated three-component reaction for the regioselective synthesis of highly functionalized pyridines: Scope, mechanistic investigations and applications
Allais, Christophe,Lieby-Muller, Frederic,Rodriguez, Jean,Constantieux, Thierry
, p. 4131 - 4145 (2013)
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. The three-component synthesis of polysubstituted pyridines starting from 1,3-dicarbonyl compounds, α,β-unsaturated carbonyl derivatives and ammonium acetate has been studied, including the scope and mechanism. This methodology is a rare example of a totally regioselective multicomponent access to highly substituted pyridines that complies with many of the stringent criteria of sustainable chemistry. Copyright
Use of β,γ-unsaturated α-ketocarbonyls for a totally regioselective oxidative multicomponent synthesis of polyfunctionalized pyridines
Allais, Christophe,Constantieux, Thierry,Rodriguez, Jean
supporting information; experimental part, p. 12945 - 12948 (2010/05/19)
Versatile partners: α-Ketocarbonyls have been shown for the first time to be versatile partners in a Michael addition promoted oxidative domino threecomponent reaction under heterogeneous conditions. This multicomponent reaction sequence led to the development of a general synthesis of highly functionalized pyridines (see scheme), allowing selective and simultaneous incorporation of a substituent at the 4-position and a synthetically useful functionality at the strategic 2-position.
