Organic & Biomolecular Chemistry 2011-07-07

Gold(III) chloride catalysed synthesis of 5-alkylidene-dihydrothiazoles.

Thomas S A Heugebaert, Leander P D Vervaecke, Christian V Stevens

Index: Org. Biomol. Chem. 9(13) , 4791-4, (2011)

Full Text: HTML

Abstract

A two step synthesis of dihydrothiazoles is presented. First, the previously unknown N-propargylic dithiocarboimidates are produced in good yields from easily available, cheap starting materials. The subsequent gold catalysed ring closure is fast and efficient, leading to dihydrothiazoles through a cascade of 5-exo-dig cyclisation and 1,3-alkyl migration. The yields range from 74% to 95%.