Simple synthesis of imidazo[1,2-A]pyridine derivatives bearing 2-aminonicotinonitrile or 2-aminochromene moiety

Arslane-Larbi Haouchine (1) , Youssef Kabri (2) , Saleha Bakhta (1) , Christophe Curti (2) , Bellara Nedjar-Kolli (1) , Patrice Vanelle (2)

1 USTHB - Université des Sciences et de la Technologie Houari Boumediene = University of Sciences and Technology Houari Boumediene [Alger]
2 ICR - Institut de Chimie Radicalaire

A simple and general method for the synthesis of new imidazopyridines bearing an aminopyridinyl, chromenyl, or quinolinyl moiety in the C2 position was developed. The Knoevenagel reaction between imidazo[1,2-a]pyridine-2-carbaldehyde 1 and malononitrile resulted in the formation of starting material 2. Subsequently, intramolecular cyclization between the cyano group of 2 and acetophenones, naphtols, hydroxyquinolines, or phenols, gave 3, 4, 5, and 6 compounds, respectively. This is a simple, reproducible, and environmentally friendly method of synthesizing substituted imidazopyridines using water as a solvent or under solvent-free conditions. [GRAPHICS] .

Domaines: Chimie

Arslane-Larbi Haouchine, Youssef Kabri, Saleha Bakhta, Christophe Curti, Bellara Nedjar-Kolli, et al.. Simple synthesis of imidazo[1,2-A]pyridine derivatives bearing 2-aminonicotinonitrile or 2-aminochromene moiety. Synthetic Communications, 2018, 48 (17), pp.2159--2168. ⟨10.1080/00397911.2018.1479759⟩. ⟨hal-02091925⟩