A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides

Koravangala S. Vinay Kumar, Toreshettahally R. Swaroop, Narasimhamurthy Rajeev, Ajjampura C. Vinayaka, Gejjalagere S. Lingaraju, Kanchugarakoppal S. Rangappa*, Maralinganadoddi P. Sadashiva*

*Department of Studies in Chemistry, University of Mysore, Mysuru, Karnataka, India, Email: mpsadashivagmail.com, rangappaksgmail.com

K. S. V. Kumar, T. R. Swaroop, N. Rajeev, A. C. Vinayaka, G. S. Lingaraju, K. S. Rangappa, M. P. Sadashiva, Synlett, 2016, 27, 1363-1366.

DOI: 10.1055/s-0035-1561391

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Abstract

An efficient modified van Leusen strategy provides biologically significant 5-substituted oxazoles in high yield using (het)aryl methyl alcohols or benzyl bromides as precursors with tosylmethylisocyanide (TosMIC) under basic conditions. This method takes place under mild reaction conditions, and tolerates various functional groups.

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Key Words

Van Leusen Oxazole Synthesis, TosMIC, T3P®, DMSO, NaHCO₃

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ID: J60-Y2016