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

Abstract : 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] .
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https://hal-amu.archives-ouvertes.fr/hal-02091925
Contributor : Didier Gigmes <>
Submitted on : Saturday, April 6, 2019 - 5:18:35 PM
Last modification on : Sunday, April 7, 2019 - 1:22:51 AM

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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⟩

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