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Synthesis 2000; 2000(14): 2019-2028
DOI: 10.1055/s-2000-8722
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High-Yield Synthesis of Novel Imidazoles and Triazoles from Alcohols and Phenols

Vincent C. O. Njar*
  • *Department of Pharmacology and Experimental Therapeutics, School of Medicine, University of Maryland, Baltimore, MD 21201-1559, USA; Fax +1(410)7 06 00 32; E-mail: vnjar001@umaryland.edu
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Publication History

Publication Date:
31 December 2000 (online)

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A variety of alcohols and phenols are converted into their corresponding imidazoles and triazoles in high yields by a facile reaction with N,N 1-carbonyldiimidazole (CDI) or N,N 1-carbonylditriazole (CDT) in acetonitrile. The reactions of allylic alcohols, enols and phenols with CDI or CDT are unprecedented. Evidence is provided which suggests that the reaction with alcohols proceeds via the corresponding carbamates by an SNi mechanism.

alcohols - imidazoles - triazoles - carbonyl diazole reagents - subsitution nucleophilic internal reaction - steroids - retinoids - heterocycles

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