Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide

Derek M. Wolfe; Peter R. Schreiner

doi:10.1055/s-2007-983740

PAPER

Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide

Derek M. Wolfe^a,b, Peter R. Schreiner*^a,b
^a Institut für Organische Chemie, Justus-Liebig-Universität, Heinrich-Buff-Ring 58, 35392 Gießen, Germany
Fax: +49(641)9934309; e-Mail: prs@org.chemie.uni-giessen.de;
^b Department of Chemistry, University of Georgia, 1001 Cedar St., Athens, GA 30602, USA
Fax: +1(706)5429454; e-Mail: prs@chem.uga.edu;

Abstract

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Abstract

Glycine was acylated with isothiocyanates and condensed to 3-alkyl 2-thiohydantoins, which were reduced with a mixture of sodium borohydride and lithium chloride and dehydrated to 1-alkyl imidazole-2-thiones. These were oxidatively desulfurized to imidazoles with benzoyl peroxide. No chromatography was required for model compounds. The methods developed were used to elaborate tyrosine to 1,4-di(p-methoxybenzyl)imidazole, a common intermediate in the syntheses of three imidazoles from the sponge Leucetta.

Key words

desulfurization - heterocycles - imidazoles - natural products - oxidation

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References

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