Bulletin of the Chemical Society of Japan

Formation and reaction of oxazoles. Synthesis of N-substituted 2-(aminomethyl) oxazoles

T Ibata, Y Isogami

Index: Ibata, Toshikazu; Isogami, Yasushi Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 2 p. 618 - 620

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Citation Number: 5

Abstract

The BF 3-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 ammonium salts bearing a 2- ...