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Synthesis 1991; 1991(9): 709-713
DOI: 10.1055/s-1991-26552
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An Efficient Procedure for the 1-Alkylation of 2-Nitroimidazoles and the Synthesis of a Probe for Hypoxia in Solid Tumours

Anthony Long* , John Parrick, Richard J. Hodgkiss
  • *Molecular Probes Unit, Chemistry Department, Brunel University, Uxbridge, Middlesex, UB8 3PH, England
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Publication Date:
29 April 2002 (online)

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The N-alkylation of 2-nitroimidazole through its 'naked' anion, formed from its alkali metal salts in the presence of crown ethers and in homogeneous solution, is shown to be a useful preparative procedure. The reactions of α,ω-dihaloalkanes can be controlled to afford either the mono- or diheteroarylalkane. The procedure has been used to alkylate theophylline and to prepare a compound of use as a probe to identify, locate and quantify hypoxia in sections from solid tumours.