ニトロフラン誘導体の合成研究(第10報) : 2-(4-Bromo-3-oxo-1-butenyl)-5-nitrofuranおよびその誘導体の合成

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Both 2-(4-bromo-3-oxo-1-butenyl)-5-nitrofuran (III) and 2-(4,4-dibromo-3-oxo-1-butenyl)- 5-nitrofuran (IV) were synthesized by bromination of 2-(3-oxo-1-butenyl)-5-nitrofuran (II) in acetic acid or chloroform, blowing off the formed hydrogen bromide by nitrogen gas stream. To avoid the formation of IV, diethyl 3-(5-nitro-2-furyl)acryloylmalonate (I) was brominated under the same conditions as described above, followed by acid catalyzed hydrolysis, and III was obtained with a small amount of its isomer, 2-(2-bromo-3-oxo-1-butenyl)-5 nitrofuran (VI). In these cases, the addition reaction of bromine or hydrogen bromide to the double bond was not observed. III was reacted with hydrochloric acid and acetic acid in the pre-sence of guanidine carbonate to give 2-(4-chloro-3-oxo-1-butenyl)-5-nitrofuran (X) and 2-(4-acetyloxy-3-oXo-1-butenyl)-5-nitrofuran (XI) respectively. Their antimicrobial activities were presented.
公益社団法人日本薬学会の論文
1967-03-25