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Licensed Unlicensed Requires Authentication Published by De Gruyter May 28, 2018

A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin

Mervat S. Sammor, Mustafa M. El-Abadelah, Ahmad Q. Hussein, Firas F. Awwadi, Salim S. Sabri and Wolfgang Voelter

Abstract

The reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines (1) with ninhydrin in dichloromethane at room temperature delivered good yields of the respective 2-hydroxy-2-(imidazo[1,5-a]pyridine-1-yl)indene-1,3-diones. In the presence of dimethyl acetylenedicarboxylate (DMAD), this uncatalyzed electrophilic substitution reaction, involving C-1 (in 1) and the central C=O (in ninhydrin), takes precedence over the three-component 1,4-dipolar cycloaddition reaction. This selectivity is probably due to the higher electrophilicity of the carbonyl carbon-2 in ninhydrin as compared to that of the sp-carbon atoms in DMAD, augmented with the high nucleophilicity of carbon-1 in 1.

Acknowledgement

Authors thank the Deanship of Scientific Research at the University of Jordan, Amman, Jordan, for financial support.

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Received: 2018-02-16
Accepted: 2018-04-22
Published Online: 2018-05-28
Published in Print: 2018-06-27

©2018 Walter de Gruyter GmbH, Berlin/Boston