Issue 21, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

A novel synthesis of imidazolesvia the cycloaddition of nitrile ylides to their imidoyl chloride precursors

Paul W. Groundwater,*a   Ian Garnett,a   Andrew J. Morton,b   Toqir Sharif,b   Simon J. Coles,c   Michael B. Hursthouse,c   Miklos Nyerges,d   Rosaleen J. Anderson,a   David Bendell,a   Alexander McKillop†a  and  Weimin Zhanga  

* Corresponding authors

a Institute of Pharmacy, Chemistry and Biomedical Sciences, School of Sciences, University of Sunderland, Sunderland, UK

b Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff, UK

c EPSRC X-Ray Crystallography Service, Department of Chemistry, University of Southampton, Highfield, Southampton, UK

d Research Group of the Hungarian Academy of Sciences, Department of Organic Chemical Technology, Technical University of Budapest, H-1521 Budapest, P.O.B. 91, Hungary

Abstract

Generation of nitrile ylides, 4 and 22, via the base-catalysed 1,3-dehydrochlorination of imidoyl chlorides, 3 and 21, gives the imidazoles, 13, 23 and 24. These imidazoles are formed by the cycloaddition of the nitrile ylides, 4 and 22, to their precursor imidoyl chlorides, 3 and 21, and the observed regiochemistry of this cycloaddition has been rationalised by energy calculations on the frontier molecular orbitals of these reactants using semi-empirical (MOPAC PM3) methods.

Graphical abstract: A novel synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors

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Article information

DOI
https://doi.org/10.1039/B104130B
Article type
Paper
Submitted
04 May 2001
Accepted
11 Sep 2001
First published
04 Oct 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2781-2787

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A novel synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors

P. W. Groundwater, I. Garnett, A. J. Morton, T. Sharif, S. J. Coles, M. B. Hursthouse, M. Nyerges, R. J. Anderson, D. Bendell, A. McKillop and W. Zhang, J. Chem. Soc., Perkin Trans. 1, 2001, 2781 DOI: 10.1039/B104130B

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