本项目在前期钯催化偶联反应系统研究工作的基础上，拟通过无催化剂条件下三炔或四炔形成的芳炔中间体与亲核试剂、双烯、叠氮、自由基试剂等反应方法对一锅法构筑多官能化复杂芳香功能化合物进行研究。探索利用Hexadehydro-Diels-Alder (HDDA)环加成串联反应形成新C-C/C-N/C-X键的偶联反应的变化规律，探索一锅方法经由高效串联的加成-环化-消去-重排途径合成多官能化复杂芳香功能化合物的新方法及其适应性，开发出性能优良的且具有较广泛用途的复杂芳香功能化合物体系。同时深入探索反应底物结构对形成产物结构影响因素及规律性，探索电子、立体因素和区域选择性对串联反应的影响并揭示其规律性，为串联环化反应的机制研究及合成具有多官能化稠环化合物的药物分子设计奠定基础以及利用HDDA/胺化反应等专一性地简洁构建多个类型的天然产物骨架分子提供新的思路。因此项目具有一定的理论意义和潜在应用价值。

The project is based on the prophase series of work about palladium-catalyzed cross-coupling reaction. We will develop aryne intermediates and nucleophilic reagent,dienes,azide,radical to construct sevaral complex system of multifunctionalized aromatic compounds under free-catalyst. Study on novel Hexadehydro-Diels-Alder (HDDA) cycloaddition cascade reaction and rules of the coupling reaction of the formation of new C-C/C-N/C-O/C-X bond. To explore a new method of one-pot synthesis of functionalized polycyclic compounds via addition-cyclization-elimination-rearrangement and its adaptability. Developed the excellent performance system in relation to synthesis of multifunctinalized complex functional aromatic compound. Meanwhile, the effective factors and the correlative regularity of what substrate structure influence on products strusture are seeken for. Exploring how some factors such as electronic effect,steric effect and the regioselectivity influence the cascade reaction. The study of the HDDA reaction mechanism of tandem sequence reaction and synthesis of multifunctional polycyclic compound provide new ways for molecular drug design and construction of natural product skeleton via specificity of HDDA/amination reaction.Therefore,this research has important theoretical significance and potential application value.