Abstract
Dess-Martin periodinane (DMP), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the intramolecular cyclization of phenolic azomethines/Schiff bases at ambient temperature leading to the rapid and expeditious synthesis of substituted benzoxazoles and benzothiazoles. Furthermore, a solution-phase strategy has been developed by treating the reaction mixtures sequentially with Amberlyst A-26 thiosulfate resin and diisopropylaminomethyl resin (PS-DIEA), which remove excess reagent and byproducts, to give pure products.
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