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Synthesis 2010(3): 398-402
DOI: 10.1055/s-0029-1217136
DOI: 10.1055/s-0029-1217136
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Dess-Martin Periodinane Mediated Intramolecular Cyclization of Phenolic Azomethines: A Solution-Phase Strategy toward Benzoxazoles and Benzothiazoles
Weitere Informationen
Received
21 September 2009
Publikationsdatum:
20. November 2009 (online)
Publikationsverlauf
Publikationsdatum:
20. November 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/201003/lookinside/thumbnails/10.1055-s-0029-1217136-1.jpg)
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.
Key words
Dess-Martin periodinane - intramolecular cyclization - azomethines - benzoxazoles - benzothiazoles - solution-phase strategy
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