Synthesis of 3- morpholin-4-yl-1- (4-nitrophenyl) -5,6-dihydro -1H- pyridin-2-one

Abstract

3-Morpholin-4-yl-1-(4-nitrophenyl)-5,6-dihydro-1H-pyridin-2-one (1) is an important intermediate for the synthesis of many biologically active compounds. It was synthesized from cyclopentanone oxime (7) and 1-fluoro-4-nitrobenzene through three steps including rearrangement. Reaction, condensation and nucleophilic substitution reaction. The structure of the target compound 1 was confirmed by H NMR and MS spectrum. Introduction Cancer is a disease caused by normal cells changing so that they grow in an uncontrolled way. Although many anti-tumor drugs and surgeries are available, the slow efficacy of the anti-tumor drugs and the cancer recurrence are still problems . In recent years, there were many small molecule anticancer drugs had been reported. Among them, 3 – morpholin – 4 – y l – 1 ( 4 – nitropheny l ) – 5 , 6 – dihydro -1 H –pyridin -2 -one (1) is an significant intermediate for the synthesis of many biologically active compounds. Therefore, design and synthesis of 3morpholin -4 –y l -1 ( 4 –nitropheny l ) -5, 6-dihydro-1H-pyridin-2-one (1) derivative as small molecule inhibitors played a essential role in the study of anticancer . Many 3-morpholin-4-yl-1-(4-nitrophenyl)-5,6-dihydro-1H-pyridin-2-one (1) derivatives which exhibited potential biological activities, such as 1 ( 4 – methoxypheny l )6 ( 4 -( 2 –methy l1(2-oxopiperidin-1-yl )propan-2-yl)phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-c arboxamide (2), 6 ( 4 ( 1 –aminocy clopropy l)phenyl )1 -( 4 –methoxyphenyl )7oxo -4,5,6,7 – tetrahydro -1 H –pyrazolo [3, 4-c ] pyridine-3 carboxamide (3) , 1 ( 4 – methoxyphenyl )-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]py ridine-3-carboxamide (4), 1 – cyclopenty l3ethy l-6(4methoxypheny l)1,4, 5, 6tetrahydro7 H –pyrazolo [3, 4-c] pyridin – 7 – one (5) , 6 ( 4 (aminomethyl) phenyl) -3(4 – methoxypheny l ) -1( trifluoromethyl ) -1, 4,5,6 -tetrahydro-7 H-pyrazolo [3, 4-c] pyridin-7-one (6), these 3 – morpholin -4yl -1(4nitrophenyl )-5 , 6 –dihydro 1H -pyridin2-one (1) derivatives showed biological activity. Most of the synthetic methods of 3 – morpholin – 4 –y l -1(4 –nitrophenyl ) -5,6 –dihydro -1H –pyridin -2 -one (1) which reported in the literature have the drawbacks, such as lower yield . Cyclopentanone oxime (7) is a key intermediate for synthesizing 3 – morpholin – 4 –yl – 1 (4nitrophenyl )-5,6 –dihydro -1 H-pyridin-2-one (1). The synthesis of the target compound is necessary. The structures of representative compounds were shown in Fig. 1 and Fig 2. 4th International Conference on Machinery, Materials and Computing Technology (ICMMCT 2016) © 2016. The authors Published by Atlantis Press 766