3-Amino-6-〔1(and 2)-halo-2-(5-nitro-2-furyl)vinyl〕-1,2,4-triazineおよび3-Amino-6-〔2-(5-nitro-2-furyl)-ethynyl〕-1,2,4-triazineの合成ならびに構造-抗菌活性

抄録

Treatment of 4-(5-nitro-2-furyl)-3-buten-2-one (I) with bromine or chlorine in the presence of sodium or potassium acetate in acetic acid gave unstable addition products, 3, 4-dihalo-4-(5-nitro-2-furyl)-3-buten-2-ones, which were smoothly dehydrohalogenated with sodium or potassium acetate to afford 3-halo-4-(5-nitro-2-furyl)-3-buten-2-one (II). Amidinohydrazone (IV) of II was oxidatively cyclized with SeO₂ to afford 3-amino-6-[1-halo-2-(5-nitro-2-furyl) vinyl]-1, 2, 4-triazine (V). 3-Amino-6-[2-halo-2-(5-nitro-2-furyl) vinyl]-1, 2, 4-triazines (VIII) were prepared by oxidative cyclization of 4-halo-4-(5-nitro-2-furyl)-3-buten-2-one amidinohydrazones (VII). VII was obtained by the reaction of 4-(5-nitro-2-furyl)-3-butyn-2-one amidinohydrazone (VI) with aq. hydrogenhalide. Dehydrohalogenation of V and VIII yielded 3-amino-6-[2-(5-nitro-2-furyl) ethyl]-1, 2, 4-triazine (IX). Antimicrobial activity of V, VIII, IX and related compounds against four kinds of microorganisms is shown in Table II.