Iodine-Catalyzed C�H Functionalization of Cyclopentenedione with Benzamidine: A Double Dehydrogenative Oxidative Cyclization to Access Fused Imidazoles

Panigrahi, A and Dhineshkumar, J and Prabhu, KR (2020) Iodine-Catalyzed C�H Functionalization of Cyclopentenedione with Benzamidine: A Double Dehydrogenative Oxidative Cyclization to Access Fused Imidazoles. In: Advanced Synthesis and Catalysis .

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Abstract

A double C�H functionalization of cyclopentenedione with benzamidine hydrochloride catalyzed by iodine has been disclosed for synthesizing fused imidazole derivatives. This methodology leads to a variety of fused imidazole derivatives and requires a sub-stoichiometric amount of iodine as a catalyst and aqueous tert-butyl hydroperoxide (TBHP) as an oxidant. This reaction involves a double-cross dehydrogenative coupling (CDC) of 1,3-cyclopentenedione and benzamidine hydrochloride to form two C�N bonds in a consecutive manner within short reaction time. A plausible mechanism has been proposed based on the mass spectrometric analysis. (Figure presented.). © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Item Type:	Journal Article
Publication:	Advanced Synthesis and Catalysis
Publisher:	Wiley-VCH Verlag
Additional Information:	The copyright for this article belongs to Wiley-VCH Verlag
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	03 Nov 2021 10:29
Last Modified:	03 Nov 2021 10:29
URI:	http://eprints.iisc.ac.in/id/eprint/65438

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