One-Pot Thiazoline Synthesis

One-Pot Thiazoline Synthesis

Author: ChemistryViews.org

Thiazolines and their derivatives are common structures in natural products and bioactive compounds. They appear, for example, in the luminescent luciferin of fireflies or in antiretrovirals such as ritonavir. A commonly used method to synthesize thiazolines is the condensation of β-aminothiols with acids, esters, or nitriles. However, only a limited range of β-aminothiols are available, which limits the scope of the method.

Wei Li and colleagues, University of Toledo, OH, USA, have developed a one-pot strategy for the synthesis of thiazoline derivatives (pictured) starting from readily available alkenes and thioamides. The team first converted an alkene to the corresponding 1,2-dibromoalkane using LiBr and urea hydrogen peroxide (UHP). The nucleophilic addition of a thioamide to the dibromoalkane then led to the desired thiazoline derivative. Since both processes use the same solvent, namely acetonitrile (CH3CN), the synthesis can be performed as a one-pot procedure.

The reaction proceeds in good yields and tolerates a wide range of functional groups. The thiazoline products can be further transformed into thiazoles or β-aminothiols.


 

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