Issue 2, 2004
From the journal:

New Journal of Chemistry

Zinc(ii) mediated synthesis of an N-substituted 2-(2-pyridyl)imidazole from a 1,2-diketone and 2-(aminomethyl)pyridine and its ligational behaviour

Michael G. B. Drew,a   Derek A. Tocher,b   Kiranmoy Chowdhury,c   Shubhamoy Chowdhuryc  and  Dipankar Datta*c  

* Corresponding authors

a Department of Chemistry, University of Reading, Whiteknights, Reading, UK

b Department of Chemistry, University College London, 20 Gordon Street, London, UK

c Department of Inorganic Chemistry, Indian Association for the Cultivation of Science, Calcutta, India
E-mail: icdd@mahendra.iacs.res.in

Abstract

Reaction of anhydrous ZnCl2 with the 1∶2 condensate (L) of benzil and 2-(aminomethyl)pyridine in methanol gives monomeric ZnL′Cl2 (1) where L′ is 2-[(4,5-diphenyl-2-pyridin-2-yl-1H-imidazol-1-yl)methyl]pyridine. In the X-ray crystal structure, 1 is found to contain tetrahedral zinc with an N2Cl2 coordination sphere and the N-substituent methylpyridine fragment hanging as a free arm. A tentative mechanism is proposed for the zinc mediated conversion of L → L′. Demetallation of 1 by the action of aqueous NaOH yields L′ in the free state. When L′ is reacted with Zn(ClO4)2·6H2O in a 1∶2 molar proportion, [Zn(L′)2]n(ClO4)2n·(H2O)n/2·(CH2Cl2)n/2 (2) is obtained. The zinc atom in 2, as revealed by X-ray crystallography, has a trigonal bipyramidal N5 coordination sphere. There are two independent ligands in the asymmetric unit of 2. One of them bonds only to one zinc atom in a bidentate mode with the N-substituent methylpyridine hanging free while the other ligand binds to two different zinc atoms in a tridentate fashion, employing the N-substituent methylpyridine nitrogen atom to form the polymeric one-dimensional chain cation.

Graphical abstract: Zinc(ii) mediated synthesis of an N-substituted 2-(2-pyridyl)imidazole from a 1,2-diketone and 2-(aminomethyl)pyridine and its ligational behaviour

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Article information

DOI
https://doi.org/10.1039/B308294F
Article type
Paper
Submitted
16 Jul 2003
Accepted
17 Oct 2003
First published
19 Jan 2004

New J. Chem., 2004,28, 323-325

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Zinc(II) mediated synthesis of an N-substituted 2-(2-pyridyl)imidazole from a 1,2-diketone and 2-(aminomethyl)pyridine and its ligational behaviour

M. G. B. Drew, D. A. Tocher, K. Chowdhury, S. Chowdhury and D. Datta, New J. Chem., 2004, 28, 323 DOI: 10.1039/B308294F

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