Synthesis Of Phthalimides And Indole-3-carbaldehydes

As the main representative of indoles,phthalimides and indole-3-carbaldehydes are pharmacologically important components of numerous biologically active natural products and medicinally significant compounds,they are also widely used for organic synthesis as intermediates and playing irreplaceable roles in many areas.The dissertation firstly described a simple operational,high yield and moderate catalytic oxidational system by using Cu(OAc)2 and 02 together to synthesis phthalimides efficiently,plurinatality and high selectivity.And then we explored the reaction of 2-ethynyanilines leading to indole-3-carbaldehydes by using N,N-Dimethylformamide as the source of formyl group,palladium as catalyst,copper and oxygen as co-oxidant.1.An environmental,high efficiency copper-catalyzed oxidative cyclization reaction with many kinds of subtrates was presented.By using 4-dimethylamiopryidine as the ligand,N-(2-Ethynylbenzyl)amines could react successfully under the condition of Cu(OAc)2/O2 catalytic systems.In the process of this reaction,02 played the roles as both an oxidizing agent and a reaction partner(the oxygen atom resource of carbonyl and aldehyde).The yield of the reaction is high,and more importantly two sp3 C-H bonds in the benzyl of subtrate were oxidated and a C-C triple bond was cleavaged under the moderate temperature during the process of this reaction.This method further enriched and expanded the use of Cu(OAc)2/O2 catalytic oxidative system in synthetic organic chemistry and the synthetic methods of phthalimides.2.To be inspired by both palladium-catalyzed cyclizations of 2-ethynyaniline leading to indoles and using N,N-Dimethylformamide as the source of formyl group,we integrated the advantages of them and then explored a new and valuable method to synthsis indole-3-carbaldehydes.By using Pd(TFA)2 as the catalyst and Cu(OAc)2/O2 as the co-oxidant respectively,we can get indole-3-carbaldehydes successfully.During the reaction,C-N bond in N,N-Dimethylformamide is cleavaged to supply formyl group.Have been used in Vilsmeier-Haack reaction as the traditional methods,POCl3 is avoided in this reaction.We overcomed the disadvantages successfully,such as sensitivity to air/water and environmental pollution.