Catalyst-Controlled Regiodivergent Oxidative Annulation of 2‑Arylimidazo[1,2‑a]pyridines with Cinnamaldehyde Derivatives for Construction of Fused N‑Heterocyclic Frameworks

Catalyst-dependent regioselective oxidative annulation of 2-arylimidazo­[1,2-a]­pyridines with cinnamaldehyde derivatives to construct fused N-heterocyclic frameworks has been described. The annulation reaction afforded 5-arylnaphtho­[1′,2′:4,5]­imidazo­[1,2-a]­pyridine-6-carbaldehydes in the presen...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-09, Vol.88 (18), p.12902-12913
Main Authors: Meena, Neha, Shinde, Vikki N., Sonam, Swami, Prakash N., Rangan, Krishnan, Kumar, Anil
Format: Article
Language:English
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Summary:Catalyst-dependent regioselective oxidative annulation of 2-arylimidazo­[1,2-a]­pyridines with cinnamaldehyde derivatives to construct fused N-heterocyclic frameworks has been described. The annulation reaction afforded 5-arylnaphtho­[1′,2′:4,5]­imidazo­[1,2-a]­pyridine-6-carbaldehydes in the presence of [RhCp*Cl2]2 as catalyst while 1,7-diarylimidazo­[5,1,2-cd]­indolizine-6-carbaldehydes were obtained using Pd­(OAc)2 as catalyst. The reaction produced annulated products in good yields and exhibited broad substrate scope and excellent functional group tolerance. The method provides two different isomeric annulated products bearing an aldehyde functionality which can be elaborated into an array of functionalities leading to valuable compounds.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00717