Transition-metal-free synthesis of imidazo[2,1-b]thiazoles and thiazolo[3,2-a]benzimidazoles via an S-propargylation/5-exo-dig cyclization/isomerization sequence using propargyl tosylates as substrates.

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2014
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Abstract
A transition-metal-free route for the synthesis of several N-fused heterocycles, including thiazolo[3,2-a]benzimidazoles and imidazo[2,1-b]thiazoles, is reported. The reaction between propargyl tosylates and 2-mercaptobenzimidazoles under basic conditions results in 3-substituted thiazolo[3,2-a]benzimidazoles, in yields up to 92% in a single synthesis step. With 2-mercaptoimidazoles as the substrate, the corresponding imidazo[2,1-b]thiazoles were exclusively obtained. The transformation is considered to proceed as an intermolecular S-propargylation that is followed by 5-exo-dig ring closure and double-bond isomerization.
Reference Key
omar2014transitionmetalfreethe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Omar, Mohamed A;Frey, Wolfgang;Conrad, Jürgen;Beifuss, Uwe;
Journal The Journal of organic chemistry
Year 2014
DOI
10.1021/jo501980w
URL
Keywords
giardiacidal compounds giardiasis inhibition enzyme omeprazole analogs

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