Article ID Journal Published Year Pages File Type
5277772 Tetrahedron Letters 2006 4 Pages PDF
Abstract

A convenient route to 4-phenyl-5-aminothiazoles is described, which offers control over substitution at the 2-position. 2-N-Acylglycinamides were dithionated and a subsequent TFAA-mediated cyclisation step was followed by removal of the 5-N-trifluoroacetyl group providing the free amines. Though applicable generally the method was found to be most effective when introducing aromatic substituents at the 2-position, whereupon moderate overall yields of the 5-amino compounds were obtained.

Graphical abstractA series of 2-N-acylglycinamides was converted into differently 2-substituted-5-aminothiazoles by treatment with Lawesson's reagent followed by TFAA-mediated cyclisation and subsequent hydrolysis of the trifluoroacetamide.Download full-size image

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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