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Paper | Regular issue | Vol 26, No. 4, 1987, pp.1015-1028
Published online, 1st January, 1970
DOI: 10.3987/R-1987-04-1015
Cyclization of C- and O-Acyl Derivatives of p-Toluamide O-Acetoacetyloxime

Etsuko Kawashima, Yuko Ando, Katsumi Tabei, and Hiroshi Miyamae

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Reaction of p-toluamide 0-acetoacetyloxime (1) with acyl chloride (2) in the presence of basic catalyst gave the corresponding 0- and C-acyl derivatives (3 and 4). Cyclization of 3 afforded 5-(2-acyloxypropeny1)-3-(p-toly1)-1,2,4-oxadiazole derivatives (6) and 5-acetonyl-3-(p-toly1)-1,2,4-oxadiazole (7). Cyclization of 4 gave 5-(1-acyl-2- oxopropy1)-1,2,4-oxadiazole derivatives (8), 4-[ 1-amino-1 - (p-tolyl)]methylene-3-methyl-2-isoxazolin-5-one (9) and 5-substituted 3-(p-to1yl)-1,2,4-oxadiazole derivatives (10).