2-取代环酮与芳香胺的Mannich反应

THE MANNICH REACTION OF 2-SUBSTITUTED CYCLOKETONES WITH ARYLAMINES

2－乙氧羰基环戊酮、2－乙氧羰基环己酮或2－乙酰基环己酮与w＝37％的甲醛水溶液和对位取代苯胺，在HCl－EtOH溶液中可直接发生Mannich反应，将芳氨基甲基引入2位，得到2－芳氨基甲基－2－乙氧羰基环戊酮盐酸盐、2－芳氨基甲基－2－乙氧羰基环己酮或2－芳氨基甲基－2－乙酰基环己酮，共合成11个新化合物．2－乙氧羰基环戊酮与苯亚甲基芳胺在乙醇溶液中回流，将芳氨基甲基引入5位，得到5－芳氨基苯基甲基－2－乙氧联基环戊酮．2－乙氧羰基环戊酮或2－乙氧羰基环己酮与苯亚甲基芳胺在醋酸－乙醇溶液中回流，得到5－苯亚甲基－2－乙氧羰基－1－芳氨基－1－环戊烯或2个新的5－苯亚甲基－2－乙氧羰基－1－苯氨基－1－环己烯．2－乙氧羰基环戊酮与苯亚甲基－β－萘胺在盐酸－乙醇溶液中回流，得到2，3，4，5－四氢－4－苯基－1H－苯并（f）环戊（c）喹啉－1－羧酸乙酯．用IR，1HNMR及元素分析确定了它们的结构．

In hydrochioride ethanolic solution, the Mannich reaction of 2- ethoxychrbonylcyclopentanone, 2 - ethoxycarbonyicyclohexanone or 2-acetylcyclohexanone with w = 37% formaldehyde solution and p-substitutal anilin takes place. Introducing arylaminomethylgroup into 2- position, eleven new 2- arylaminomethyl- 2- ethoxycarbonyl- cyclopentanonehydrochloride, 2- arylaminomethyl- 2 - ethoxycarbonylcyclohexanone or 2 - arylaminmethyl - 2 - acetylcyclohexanone were obtained. Refluxing of 2- ethoxycarbonyl- cyclopentanone with benzylidenearylamine in ethanolic solution, and introducing arylaminomethyl- group into 5-position,two 5 - arylaminophenylmeyl - 2 - ethoxycarbonyl - cyclopentanone were obtained. Refluxing of 2- ethoxycarbonylcyclopentanone or 2 - ethoxycarbonylcyclohexanone with benzylidenearylamine in acetic acid - ethanol solution, two 5- benzylidene- 2- ethoxycarbonyl- 1 -arylamino -1-cyclopentene and two new 5-benzyliene - 2- ethoxycarbonyl- 1 - arylamiino- 1 -cyclohexene were obtained. Refluxing of 2 - ethoxycarbonylcyclopentanone with benzylidene -β- naphthylamine in hydrochioric aed ethanol solution, ethyl 2, 3, 4, 5- tehahydro- 4phenyl- 1H- Benzot(f)cyclo - penta(c)- 1 - quinolinearboxylate was obtained. The smictthe was dedued from IR, lHNMR and fort analysis.