1965 年 85 巻 8 号 p. 744-751
Syntheses of 5-substituted-1, 3, 4-oxadiazole derivatives in various ways are described. Although 5-nitro-2-furohydrazide (I) gave 2-(5-nitro-2-furyl)-5-methyl-1, 3, 4-oxadiazole (X) by refluxing with acetic anhydride, its vinylog (II) did not yield the corresponding 1, 3, 4-oxadiazole (XIV) under the same condition. On the other hand, II gave 2-[2-(5-nitro-2-furyl) vinyl]-1, 3, 4-oxadiazole (XI) by refluxing with ethyl orthoformate, but I did not yield the corresponding compound (III) under the same condition.
2-(5-Nitro-2-furyl)-5-aryl (or furyl)-1, 3, 4-oxadiazoles and their vinylogs were obtained by refluxing of the corresponding diacylhydrazines with phosphoryl chloride in a good yield, but the yield decreased markedly when aryl or furyl group in the 5-position was replaced by an alkyl group. Antimicrobial activities of these nitrofuran compounds are presented in Tables III to V.