I2–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

Madhu Chennapuram; Narender Reddy Emmadi; Chiranjeevi Bingi; Krishnaiah Atmakur

doi:10.1039/C4RA15835K

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I₂–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones†

Madhu Chennapuram,^a Narender Reddy Emmadi,^a Chiranjeevi Bingi^a and Krishnaiah Atmakur*^ab

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* Corresponding authors

^a Division of Crop Protection Chemicals, CSIR-Indian Institute of ChemicalTechnology, Tarnaka, Hyderabad 500 007, India
E-mail: krishnu@iict.res.in
Fax: +91 40 27193382
Tel: +91 40 27191436

^b AcSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India

Abstract

A simple, highly efficient and selective oxidative cross coupling of imidazo[1,2-a]pyridine (IP) compounds (1) and methylketones (2), promoted by molecular iodine in DMSO in the presence of a catalytic amount of PTSA has been realized in a one pot reaction. This strategy has provided a general route for the synthesis of 1-aryl-2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethane-1,2-diones (3) with a new C–C bond formation through Kornblum oxidation followed by nucleophilic attack of IP compounds (1) on the in situ formed phenylglyoxal. Simple reaction conditions, no metal catalysts and selective product formation are the advantages of this protocol.

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DOI: https://doi.org/10.1039/C4RA15835K
Article type: Paper
Submitted: 05 Dec 2014
Accepted: 04 Feb 2015
First published: 05 Feb 2015

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RSC Adv., 2015,5, 19418-19425

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I₂–DMSO–PTSA: a simple and metal free oxidative cross coupling of imidazo[1,2-a]pyridines and methylketones

M. Chennapuram, N. R. Emmadi, C. Bingi and K. Atmakur, RSC Adv., 2015, 5, 19418 DOI: 10.1039/C4RA15835K

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