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New Easy Approach to the Synthesis of 2,5-Disubstituted and 2,4,5-Trisubstituted 1,3-Oxazoles. The Reaction of 1-(Methylthio)acetone with Nitriles

Antonio Herrera, Roberto Martínez-Alvarez,* Pedro Ramiro, Dolores Molero and John Almy

*Departamento de Química Orgnica, Facultad de Ciencias Químicas, Universidad Complutense, E-28040 Madrid, Spain, CAI de RMN, Facultad de Ciencias Químicas, Universidad Complutense, E-28040 Madrid, Spain, Email: rmaquim.ucm.es

A. Herrera, R. Martinez-Alvarez, P. Ramiro, D. Molero, J. Almy, J. Org. Chem., 2006, 71, 3026-3032.

DOI: 10.1021/jo052619v (free Supporting Information)


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Abstract

The reaction of 1-(methylthio)acetone with different nitriles in the presence of triflic anhydride gave 2-substituted 5-methyl-4-methylthio-1,3-oxazoles in good yield. The methylthio group at the C4 position can easily be removed with Raney nickel. 4-Methylsulfonyl derivatives were prepared by the oxidation of the MeS group with m-CPBA.

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Key Words

1,3-Oxazoles, Sulfones, Desulfurization, m-CPBA, Nickel


ID: J42-Y2006-940