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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Volume 73, Issue 6

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

Mervat S. Sammor / Mustafa M. El-Abadelah
  • Corresponding author
  • Department of Chemistry, Faculty of Science, The University of Jordan, Amman 11942, Jordan
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Ahmad Q. Hussein / Firas F. Awwadi / Salim S. Sabri / Wolfgang Voelter
  • Corresponding author
  • Interfakultäres Institut für Biochemie, Universität Tübingen, Hoppe-Seyler Straße 4, 72076 Tübingen, Germany
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2018-05-28 | DOI: https://doi.org/10.1515/znb-2018-0039

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.

Keywords: 2-hydroxy-2-(imidazo[1,5-a]pyridinyl)indenediones; electrophilic substitution; imidazo[1,5-a]pyridines; ninhydrin; X-ray structure

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About the article

Received: 2018-02-16

Accepted: 2018-04-22

Published Online: 2018-05-28

Published in Print: 2018-06-27


Citation Information: Zeitschrift für Naturforschung B, Volume 73, Issue 6, Pages 413–421, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0039.

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