ニトロフラン誘導体の合成研究(第4報) : アミド類, ヒドラジト類, ならびにシッフ塩基類の合成

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3-(5-Nitro-2-furyl) acryloyl azide (III) was synthesized by diazotization of 3-(5-nitro-2-furyl) acrylic acid hydrazide (I) or by treating 3-(5-nitro-2-furyl) acryloyl chloride (II) with sodium azide. III reacts with esters of amino acids, aliphatic aminis, and pyimidinyl-hydrazines at rooom temperature yielding the corresponding amides and hydrazides. Refluxing of N-[3-(5-nitro-2-furyl) acryloyl] glycine ethyl ester (IVa) with phosphorus pentachloride in dry chloroform give 2-[2-[5-nitro-2-furyl) vinyl]-5-ethoxy-1,3-oxazole (V). Schiff bases can be obtained by treating 1-phenyl-2-amino-1,3-propanediols or 4-phenyl-5-amino-1,3-dioxanes with 5-nitro-2-furaldehyde. Reduction of D- and L-2,2-dimethyl-4-phenyl-5-(5-nitro-2-furfurylidene) amino-1,3-dioxanes [XVa (α) and XVb (α)] with sodium borohydride to D- and L-2,2-dimethyl-4-phenyl-5-(5-nitro-2-furfuryl) amino-1,3-dioxanes was carried out readily. Antimicrobial activities of these nitrofuran compounds are presented in Table VI.
公益社団法人日本薬学会の論文
1966-04-25