Synthesis Of Three Functional Active Substances Isoindoline-1-one

Isoindoline-1-one derivatives widely exist in biological and pharmaceutical active molecules.They are useful intermediates for the synthesis of alkaloids.They are widely used in organic pigments,luminescent materials,coatings,plastics and other industrial fields.Therefore,the synthesis of these compounds has long attracted the attention of chemists.In recent years,many synthetic methods have been developed,but the synthetic methods reported in the literature usually have some disadvantages,such as harsh reaction conditions,difficult preparation of substrates,long synthetic steps,and expensive metal catalysis.Therefore,it is of great significance to develop a method with simple operation,mild reaction conditions,fast reaction rate,simple post-treatment,easy preparation of substrates and short synthesis steps.In this paper,three new methods for the synthesis of isoindoline-1-one derivatives were explored.First,a series of 3-methyl-3-methoxyisoindoline-1-one substrates were synthesized by the method of reference;second,the synthesis of chiral 3-methyl-3-methoxyisoindoline-1-one was tested;then,the synthesis of 3-methyl-3-methoxyisoindoline-1-one was used as the template reaction,and the effects of solvent,temperature,catalyst,catalyst dosage and HSi Cl₃dosage on the reaction were studied.At the same time,41 new 3-alkyl-3-alkoxyisoindoline-1-ones were obtained.Compared with the synthetic methods reported in the literature,it has the advantages of short synthetic steps,mild reaction conditions,high yield and good substrate universality.Then,a new method for the synthesis of（Z）-3-alkyleneisoindoline-1-one was explored using 2-（4-methoxyphenyl）-3-methyleneisoindoline-1-one and benzaldehyde as raw materials.The effects of solvent,feed ratio,temperature,amount of catalyst and trichlorosilane on the reaction were studied.It was found that the yield of the compound could be increased to 83%,but the universality of the substrate was not good,and the yield of other substrates was very low.Finally,the synthesis method of 2-phenylpropane-1,3-dimethylidene diisoondole-1-one was explored.2-（4-methoxyphenyl）-3-methylene diisoondoline-1-one and benzaldehyde were used as template reaction materials.The reaction conditions such as feed ratio,amount of p-toluenesulfonic acid,solvent,temperature and amount of HSi Cl₃ were optimized,and the universality of the substrate was investigated.Then,the substrate applicability of the reaction was studied,and 29 new compounds containing（3E,3’E）2-phenylpropane-1,3-dimethylene bis isoindole-1-one skeleton were constructed.These isoindoline-1-one derivatives have not been reported.