Issue 19, 2000
From the journal:

Chemical Communications

Synthesis of ene-1,1-diamines and pyrrolo[1,2-a]imidazolediones by 4,5-dihydroimidazole N-oxide cycloaddition and isoxazoline ring opening

Raymond C. F. Jones,*a   Jason N. Martin,b   Paul Smith,c   Tomas Gelbrich,d   Mark E. Lightd  and  Michael B. Hursthoused  

* Corresponding authors

a Department of Chemistry, Loughborough University, Leics., UK

b Department of Chemistry, The Open University, Walton Hall, Milton Keynes, UK

c SmithKline Beecham Pharmaceuticals, New Frontiers Science Park North, Harlow, Essex, UK

d EPSRC National Crystallography Service, Department of Chemistry, University of Southampton, Highfield, Southampton, UK

Abstract

Dihydroimidazole N-oxides 1 undergo 1,3-dipolar cycloaddition with alkyne dipolarophiles and the cycloadducts suffer isoxazoline N–O bond cleavage to afford ene-1,1-diamines, with subsequent cyclisation to pyrrolo[1,2-a]imidazole-5,6-diones if possible.

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Article information

DOI
https://doi.org/10.1039/B005530L
Article type
Communication
Submitted
10 Jul 2000
Accepted
18 Aug 2000
First published
21 Sep 2000

Chem. Commun., 2000, 1949-1950

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Synthesis of ene-1,1-diamines and pyrrolo[1,2-a]imidazolediones by 4,5-dihydroimidazole N-oxide cycloaddition and isoxazoline ring opening

R. C. F. Jones, J. N. Martin, P. Smith, T. Gelbrich, M. E. Light and M. B. Hursthouse, Chem. Commun., 2000, 1949 DOI: 10.1039/B005530L

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