| 2,3-Dihydro-1H-isoindolin-1-ones,commonly known as isoindolinone,are important nitrogen-containing heterocyclic compounds with a structural motif of benzo pyrrolidone.Isoindolinones are widely occurring as natural products such as Clitocybin,Daldinan,Pestalachloride,etc.,which have a variety of important biological activities,for example,analgesic,anti-inflammatory,antibacterial,anti-tumor,anti diabetes,anti cardiovascular diseases and other activities.Therefore,they play important roles in drug discovery.Many drugs with isoindolinone have been marketed and have played an important role in clinic,such as Falipamil,Lenalidomide,Indoprofen,etc.Up to date,many synthetic methods of isoindolinones compounds have been reported,including metal catalyzed Csp2-X coupling cyclization,metal catalyzed Csp2-H coupling cyclization one-pot,multi component method and other methods.Due to the somehow disadvantages such as:harsh reaction condition,heavy metal pollution and difficulty in substrate preparation,new methods for preparation of isoindolines are still necessary.In this thesis,we have designed an organo-catalyzed method for the synthesis of isoindolinones using 2-formylbenzonitriles and ?,?-unsaturated ketones as reacting substrates.The compounds with isoindolone structure were constructed via a tandem reaction under the mild condition with PPh3 as catalyst,and the products could be purified by recrystallization.The following topics are covered in this research work:1.Preparation of 2-formylbenzonitriles2.Optimization of reaction conditions3.Investigation of the substrate scope under the optimized condition.4.Several PD 172938 analogues have been synthesized via the organo-catalyzed method.An organo-catalyzed,mild and efficient method for the synthesis of isoindolinone compounds has been developed.The method has the advantages of environmental friendliness,mild reaction conditions,atomic economy,easy purification and further modification of products. |
PDF Full Text Request