Journal article

Publication year: 2007

Pages: 2002-2008

Journal: Synthesis: Journal of Synthetic Organic Chemistry

Volume number: 2007

Issue number: 13

ISSN: 0039-7881

DOI Link: https://doi.org/10.1055/s-2007-983740

Publisher: Thieme Publishing / Georg Thieme Verlag

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.

Harvard Citation style: Wolfe, D. and Schreiner, P. (2007) Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide, Synthesis: Journal of Synthetic Organic Chemistry, 2007(13), pp. 2002-2008. https://doi.org/10.1055/s-2007-983740

APA Citation style: Wolfe, D., & Schreiner, P. (2007). Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide. Synthesis: Journal of Synthetic Organic Chemistry. 2007(13), 2002-2008. https://doi.org/10.1055/s-2007-983740