One-Pot Thiazoline Synthesis

  • Author:
  • Published: 16 February 2017
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: One-Pot Thiazoline Synthesis

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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