3,4-二氢-2(1H)喹啉酮衍生物的合成研究

Study on the Synthesis of 3,4-dihydro-2(1H)quinolinone Derivatives

对3,4-二氢-2(1H)喹啉酮衍生物1,2,3(R= NO2,NH2,OH;R= H,NO2,NH2)的合成进行了研究。以苯胺和3-氯丙酰氯为原料,制得N-苯基-3-氯丙酰胺,然后经环合得到3,4-二氢-2(1H)喹啉酮,再经由硝化、还原、重氮化水解合成了一系列3,4-二氢-2(1H)喹啉酮衍生物:6-硝基-3,4-二氢-2(1H)喹啉酮(1a),6,8-二硝基-3,4-二氢-2(1H)喹啉酮(1b),6-氨基-3,4-二氢-2(1H)喹啉酮(2a),6,8-二氨基-3,4-二氢-2(1H)喹啉酮(2b),6-氨基-8-硝基-3,4-二氢-2(1H)喹啉酮(2c),6-羟基-3,4-二氢-2(1H)喹啉酮(3a)和6-羟基-8-硝基-3,4-二氢-2(1H)喹啉酮(3b),其中化合物(2c)及(3b)为新化合物。单步产率均在86%以上,路线简单,操作简便,反应条件温和。采用MS,1HNMR对产品进行了定性及结构表征。

A new method of synthesis 3,4-dihydro-2(1H)quinolinone derivatives was investigated with higher yield and simpler operation. Its yield of each step is between 86.5%~99.6%. The title compounds were prepared starting from aniline and 3-chloropropionyl chloride, via cyclizing, nitration, reduction, diazation and hydrolysis. They are 6-nitro-3,4-dihydro-2(1H)quinolinone, 6,8-dinitro-3,4-dihydro-2(1H) quinolinone, 6-amino-3,4-dihydro-2(1H)quinolinone, 6,8-diamino-3,4-dihydro-2(1H)quinolinone, 6-amino- 8-nitro-3, 4-dihydro-2(1H)quinolinone, 6-hydroxy-3,4-dihydro-2(1H)quinolinone and 6-hydroxy-8-nitro-3, 4-dihydro-2(1H)quinolinone. Among them, 6-amino-8-nitro-3,4-dihydro-2(1H)quinolinone and 6-hydroxy-8 -nitro-3,4-dihydro-2(1H)quinolinone are two new compounds and their synthesis method haven抰 been mentioned in literatures. All these derivatives of 3,4-dihydro-2(1H)quinolinone were characterized by MS and / or 1HNMR.