Synthesis of novel aryl-1, 2-oxazoles from ortho-hydroxyaryloximes

TJ Dale, AC Sather, J Rebek

Index: Dale, Trevor J.; Sather, Aaron C.; Rebek Jr., Julius Tetrahedron Letters, 2009 , vol. 50, # 45 p. 6173 - 6175

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Citation Number: 18

Abstract

The reaction of ortho-hydroxyaryloximes with p-toluenesulfonyl chloride in the presence of an amine base efficiently generates the corresponding aryl-1, 2-oxazole. Investigations revealed that solvent polarity greatly affected the rate of the reaction with faster rates observed in more polar solvents. The reaction proceeds to completion in only a few minutes in acetonitrile at room temperature, and the synthesis of four novel aryl-1, 2-oxazoles is ...