Formation and Reaction of Oxazoles. Synthesis of N-Substituted 2-(Aminomethyl)oxazoles

Article abstract of DOI:10.1246/bcsj.62.618

The BF3-catalyzed reaction of substituted α-diazoacetophenones with chloroacetonitrile gave 5-aryl-2-chloromethyloxazoles (3) in high yields.Methyl p-nitrophenyldiazoacetate also yielded 2-(chloromethyl)-5-methoxy-4-(p-nitrophenyl)oxazole.The nucleophilic substitution of 3 with primary, secondary, and tertiary amines afforded the corresponding secondary amines, tertiary amines, and quaternary anmmonium salts bearing a 2-oxazolylmethyl group.