Study On Synthesis Of Novel Heterocyclic Compounds Containing Phthalide - Containing

Heterocyclic chemistry has always been the focus of recent research in the field of organic synthesis and pharmaceutical chemistry. Great efforts have been paid by organic chemists for the synthesis of novel heterocyclic molecules in more efficient way, as well as the environment issues. With this context, the topic of’green’chemistry has received increasing attention during the last decade. This dissertation mainly focused on the synthesis of novel bis-heterocyclic compounds which contain phthalide-like skeletons, with the standpoint of green chemistry.A highly efficient method for the synthesis of3-(4-hydroxy)coumarinylphthalides and3-(4-hydroxy)quinolinylphthalides was developed, along with a simple and convenient process for the preparation of3-(4-aryl substituted)coumarinylphthalides via Suzuki-Miyaura coupling. Based on this result, we have successfully demonstrated an environmentally friendly, novel and highly efficient one-pot strategy for the synthesis of3-(4-hydroxy)coumarinyl-substituted isoindolinones and3-indolyl-substituted isoindolinones which are two relatively underexplored isoindolinone core structure motifs through a sequential MCRs of2-formyl benzoic acids,4-hydroxycoumarins or indoles in ammonium hydroxide. This operationally simple, practical, and scalable method allows C-C bond and C-N bond formation with excellent scope under mild conditions.Next, AgOOCCF3-promoted divergent approach to polysubstituted indoles was developed, with which we could readily obtain the expected indole derivatives in good yield. In addition, a highly efficient and convenient approach for the synthesis of series of3-triazolyphthalides via Click chemistry was described.By employing the method we developed, a series of3-indolyl-substituted benzoboroxoles were obtained with carrying out the reactions of indoles and2-formylphenylboronic acid in water.