Tetrahedron letters

Thioamides via thiatriazolines

RV Kolakowski, N Shangguan, LJ Williams

Index: Kolakowski, Robert V.; Shangguan, Ning; Williams, Lawrence J. Tetrahedron Letters, 2006 , vol. 47, # 7 p. 1163 - 1166

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Citation Number: 22

Abstract

Thioamides serve as isosteric replacements for amides and as versatile synthetic precursors to thiazolines and thiazoles. 1 Most approaches to the construction of thioamides involve formation of the parent amide followed by thionation. 2 Recently, we showed that thioacids and azides form amides in a base-promoted reaction: 3 and 4 the azide and thioacid appear to couple directly to form a thiatriazoline and then fragment to form amide, N 2 , and S 8 products (Eq. 1, X = ...