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: rma
quim.ucm.es
A. Herrera, R. Martinez-Alvarez, P. Ramiro, D. Molero, J. Almy, J. Org. Chem., 2006, 71, 3026-3032.
DOI: 10.1021/jo052619v
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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
