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Org Biomol Chem. 2016 Jun 14;14(22):5073-8. doi: 10.1039/c6ob00656f. Epub 2016 May 16.

Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines.

Organic & biomolecular chemistry

Sadhanendu Samanta, Sourav Jana, Susmita Mondal, Kamarul Monir, Swapan K Chandra, Alakananda Hajra

Affiliations

  1. Department of Chemistry, Visva-Bharati (A Central University), Santiniketan, 731235, West Bengal, India. [email protected].

PMID: 27182027 DOI: 10.1039/c6ob00656f

Abstract

A unique copper-catalyzed binucleophilic switching of 2-aminopyridine has been developed for the regioselective synthesis of 2- and 3-iodoimidazo[1,2-a]pyridines using alkenes/alkynes as coupling partners in the presence of molecular iodine under aerobic reaction conditions. This method was also applied to the synthesis of 2-iodo-3-phenylbenzo[d]imidazo[2,1-b]thiazoles. This protocol offers an easy route towards the synthesis of 2,3-diarylimidazo[1,2-a]pyridines.

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