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Synfacts 2006(7): 0663-0663  
DOI: 10.1055/s-2006-941847
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,5- and 2,4,5-Substituted 1,3-Oxazoles

Contributor(s): Victor Snieckus, Todd Macklin
A. Herrera, R. Martínez-Alvarez, P. Ramiro, D. Molero, J. Almy*
Universidad Coplutense, Madrid, Spain and California State University, Turlock, USA
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

The reported procedure provides a general approach to the synthesis of 2-substituted 5-methyl-4-(methylthio)oxazoles under mild conditions in good yields. The nature of the cyano group does not significantly affect the yields of the reaction and the product thiomethyl group may be reductively cleaved by Raney nickel (86-93%) or oxidized to a methylsulfonyl group by MCPBA (91-97%). The intermediacy of an α-trifloyl species in this reaction is suggested by spectroscopic evidence.