Metal‐Free Michael‐Addition‐Initiated Three‐Component Reaction for the Regioselective Synthesis of Highly Functionalized Pyridines: Scope, Mechanistic Investigations and Applications. Issue 19 (15th May 2013)

• Record Type: Journal Article
• Authors: Allais, Christophe; Liéby‐Muller, Frédéric; Rodriguez, Jean; Constantieux, Thierry
• Is Part Of: European journal of organic chemistry. Issue 19(2013)
• Page Start: 4131
• Page End: 4145
• Publication Date: 2013-05-15
• Subjects: Nitrogen heterocycles -- Multi­component reactions -- Michael addition -- Reaction mechanisms -- Heterogeneous catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300246
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : 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.