Sustainable Synthesis of Thioimidazoles via Carbohydrate-Based Multicomponent Reactions

The synthesis of diversely functionalized thioimidazoles through a modern variant of the Marckwald reaction is presented. This new protocol utilizes unprotected carbohydrates as well as simple amine salts as sustainable and biorenewable starting materials. Importantly it was discovered that a bifurcated reaction pathway results from using aldoses and ketoses respectively, yielding distinct reaction products in a highly selective manner.