Study On The Novel Synthsis Of Naphthoquinolizinones And Naphthopyrans Via Rhodium(?) Catalyzed C–H Bond Activation

Due to its diverse biological activity and distinctive photoelectric properties,fused heterocyclys are widely used in the fields of drug synthesis,pesticides,and material chemistry.In view of their significance,the synthesis of heterocyclic compounds has attracted extensive attention.How to easily and efficiently synthesize fused heterocyclys is one of the important and challenging research areas in the field of synthetic chemistry.On the other hand,transition metal-catalyzed C–H bond functionalization is widely used as a highly efficient and economical synthesis for the construction of C–C and C–hetero bond.Recently,the transition metal-catalyzed C–H bond carbenoid insertion has gradually become a common organic synthesis method due to its high reactivity,good selectivity,mild conditions,and eco-friendly,and it has been widely used in the synthesis of heteroaromatic compounds.Based on the above background,this dissertation designed and developed a novel synthesis of naphthoquinolizinones and naphthopyrans through Rh-catalyzed C–H carbenoid insertion.The main content summarized in three aspects as follows.Chapter 1: ReviewIn this chapter,the progresses of transition metal catalyzed C–H bond activation reaction and Rh-catalyzed C–H bond carbenoid insertion reaction are introduced.Chapter II: Study on the Novel Synthesis of NaphthoquinolizinonesThis chapter systematically studied the novel synthesis of naphthoquinolizinones via Rh(?)-catalyzed of 2-aryl-3-cyanopyridine with ?-carbonyldiazo compounds.It turned out that the reaction through Rh(?)-catalyzed double C–H bond carbenoid insertion and annulations of 2-aryl-3-cyanopyridines with ?-diazo carbonyl compounds could selectively afford naphthoquinolizinones with either an amine or an amide attached on 11-position by simply turning the nature of solvent and additive used.This new protocol provides a simple,efficient approach toward naphthoquinolizinones.Chapter 3: Study on the Novel Synthesis of NaphthopyransIn this chapter,the novel synthesis of naphthopyrans via Rh(?)-catalyzed of 2-substituted acetophenone with cyclic 2-diazo-1,3-dicarbonyl compounds.It turned out that the reaction through Rh(?)-catalyzed double C–H bond carbenoid insertion and annulations of 2-substituted acetophenone with cyclic 2-diazo-1,3-dicarbonyl compounds could efficiently afford naphthopyrans with different substitution groups.The multi-step tandem reaction provides an economical and an efficient way to synthesized naphthopyrans.