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DOI: 10.1055/s-2007-983740
Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide
Publication History
Publication Date:
18 June 2007 (online)
![](https://www.thieme-connect.de/media/synthesis/200713/lookinside/thumbnails/10.1055-s-2007-983740-1.jpg)
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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