The Journal of organic chemistry

Synthesis of γ-azido-β-ureido ketones and their transformation into functionalized pyrrolines and pyrroles via Staudinger/Aza-Wittig reaction

AA Fesenko, AD Shutalev

Index: Fesenko, Anastasia A.; Shutalev, Anatoly D. Journal of Organic Chemistry, 2013 , vol. 78, # 3 p. 1190 - 1207

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Citation Number: 19

Abstract

A simple two-step procedure yielding γ-azido-β-ureido ketones or/and their cyclic isomers, 6- (1-azidoalkyl)-4-hydroxyhexahydropyrimidin-2-ones, has been developed. The synthesis includes three-component condensation of acetals of 2-azidoaldehydes with urea or methylurea and p-toluenesulfinic acid in aqueous formic acid followed by reaction of the obtained N-[(2-azido-1-tosyl) alkyl] ureas with sodium enolates of α-functionalized ketones ...