The Journal of organic chemistry

Monosubstituted Oxazoles. 1. Synthesis of 5-Substituted Oxazoles by Directed Alkylation

CM Shafer, TF Molinski

Index: Shafer, Cynthia M.; Molinski, Tadeusz F. Journal of Organic Chemistry, 1998 , vol. 63, # 3 p. 551 - 555

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Citation Number: 40

Abstract

A general method is presented for synthesis of 2-(methylthio)-5-substituted oxazoles 2. Deprotonation of the readily available 2-(methylthio) oxazole (1) with n-BuLi occurs smoothly in the presence of TMEDA and regiospecifically at C5. The organometallic 1a added rapidly to aldehydes and other electrophiles to provide 5-substituted-2-(methylthio) oxazoles in very good to excellent yields. Reductive removal of the MeS group gave the ...