フラン誘導体の合成化学的研究(第34報) : 2,3-Bis(5-nitro-2-furyl)pyrazine誘導体の合成

抄録

Air oxidation of 2, 3-bis(2-furyl)-5, 6-dihydropyrazine (I) and 2, 3-bis(2-furyl)-5-methyl-5, 6-dihydropyrazine (II) in ethanol, with application of potassium cyanide, afforded 5, 6-bis-(2-furyl)-2-pyrazinamide (III) from I and 5, 6-bis(2-furyl)-3-methyl-2-pyrazinamide (IV) from II, both in a good yield. Hydrolysis of III and IV, followed by esterification and nitration respectively gave ethyl 5, 6-bis(5-nitro-2-furyl)-2-pyrazinoate(XIII) and ethyl 5, 6-bis(5-nitro-2-furyl)-3-methyl-2-pyrazinoate (XIV), which were respectively hydrolyzed to the corresponding carboxylic acids (XV and XVI). On the other hand, air oxidation of I and II in alkaline solution gave the corresponding pyrazines which were respectively nitrated to 2, 3-bis(5-nitro-2-furyl)pyrazine (VII) and 2, 3-bis(5-nitro-2-furyl)-5-methylpyrazine (VIII). A total of 11 kinds of amine derivatives were prepared from XIII, XIV, XV, and XVI. Antibacterial activity of these compounds was examined and several of them showed antibacterial activity approximately equal to that of 3-(5-nitro-2-furyl)acylamide.