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Updated: Jan 18, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Isoxazoles to Multisubstituted Thiazoles via an Ammonium Iodide-Catalyzed Formal [3+2] Cycloaddition Reaction
Junzheng Sun1, Wenjing Yang1, Fengshi Sun1
1National Key Laboratory of Advanced Drug Delivery and Release Systems, School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, P. R. China.
Abstract:
A method for the conversion of isoxazoles into thiazoles by skeleton rearrangement has been achieved by an ammonium iodide-catalyzed cycloaddition protocol under mild conditions with a broad substrate scope and good functional group tolerance. Most appealingly, the reaction can proceed smoothly without the addition of any transition metal catalyst. Detailed mechanistic studies, including control experiments and key reaction intermediate characterization, reveal an intermolecular [3+2] cycloaddition reaction pathway. We also demonstrated the synthetic utility on a preparative-scale trisubstituted thiazole for diverse downstream transformations, including the synthesis of several bioactive molecules.
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