Liquid-Phase Organic Synthesis of Thiazoles Using Poly(ethylene glycol)–Bound Sulfonyl Chloride Resin

Abstract

Reaction of poly(ethylene glycol) (PEG)–bound sulfonic acid with thionyl chloride formed difunctionalized PEG-bound sulfonyl chloride, which was treated with α-hydroxyketones, followed by treatment with thioamides in the presence of potassium carbonate, to afford thiazoles in good yields with a facile workup procedure.

Keywords:

• Liquid-phase organic synthesis
• PEG-bound sulfonyl chloride
• thiazole

ACKNOWLEDGMENT

We gratefully acknowledge financial support from the National Natural Science Foundation NSF of China (No. 20562005) and NSF of Jiangxi Province (Nos. 0620021 and 2007GZW0185).

Notes

^a Yields refer to the isolated pure products based on PEG-bound disulfonyl chloride.

^b With the first regenerated resin.

^c With the second regenerated resin.

^d With the fourth regenerated resin.