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

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

Organic & biomolecular chemistry (2011-05-17)
Thomas S A Heugebaert, Leander P D Vervaecke, Christian V Stevens
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%.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Gold(I) chloride, 99.9% trace metals basis
Sigma-Aldrich
Gold(III) chloride, ≥99.99% trace metals basis
Sigma-Aldrich
Gold(III) chloride, 99%