Dess-Martin Periodinane Mediated Intramolecular Cyclization of Phenolic Azomethines: A Solution-Phase Strategy toward Benzoxazoles and Benzothiazoles

D. Subhas Bose*, Mohd. Idrees

*Organic Chemistry Division III, Fine Chemicals Laboratory, Indian Institute of Chemical Technology, Hyderabad, Tarnaka 500 007, India, Email: dsbiict.res.in

D. S. Bose, M. Idrees, Synthesis, 2010, 398-402.

DOI: 10.1055/s-0029-1217136

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Abstract

Dess-Martin periodinane (DMP) efficiently mediates the intramolecular cyclization of phenolic azomethines at ambient temperature leading to substituted benzoxazoles and benzothiazoles. Treatment of the reaction mixtures sequentially with Amberlyst A-26 thiosulfate resin and diisopropylaminomethyl resin (PS-DIEA) removes excess reagent and byproducts, to give pure products.

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proposed mechanism

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Hypervalent Iodine Mediated Intramolecular Cyclization of Thioformanilides: Expeditious Approach to 2-Substituted Benzothiazoles

D. S. Bose, M. Idrees, J. Org. Chem., 2006, 71, 8261-8263.

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Key Words

Dess-Martin periodinane, intramolecular cyclization, azomethines, benzoxazoles, benzothiazoles, solution-phase strategy

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ID: J66-Y2010-0310