Regioselective competitive synthesis of 3,5-bis(het) aryl pyrrole-2-carboxylates/carbonitriles vs. β-enaminones from β-thioxoketones

Sharath Kumar, KS and Ananda, H and Rangappa, S and Raghavan, SC and Rangappa, KS (2021) Regioselective competitive synthesis of 3,5-bis(het) aryl pyrrole-2-carboxylates/carbonitriles vs. β-enaminones from β-thioxoketones. In: Tetrahedron Letters .

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Abstract

An easily adaptable protocol for the synthesis of 3,5-bis(het)aryl-2-carboxylate/nitrile pyrroles and the related 2,3,5-tri(het)aryl-pyrroles with complementary regioselectivity from the corresponding 1,3-bis(het)aryl-1,3-monothio diketones or β-enaminone precursors has been reported. Initially, regioselective base catalyzed condensation of glycine ethyl/methyl esters or aminoacetonitrile with 1,3-bis(het)aryl-1,3-monothio diketones give β-enaminones, which then in-situ undergoes cyclization to form 3,5-bis(het)aryl-2-carboxylate/nitrile pyrroles. The synthesis of 2,3,5 tri substituted pyrroles with full control over 3rd & 5th position on pyrrole ring is the noteworthy feature of this protocol. Although the product yields are moderate to good, the method offers a facile regioselective entry to 2,3,5 trisubstituted pyrroles without the aid of transition metal. © 2021 Elsevier Ltd

Item Type:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsevier Ltd
Additional Information:	The copyright for this article belongs toElsevier Ltd
Department/Centre:	Division of Biological Sciences > Biochemistry
Date Deposited:	28 Nov 2021 10:20
Last Modified:	28 Nov 2021 10:20
URI:	http://eprints.iisc.ac.in/id/eprint/70313

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