Study On Copper Catalyzed The Synthesis Of Quinoline And 2-carbonyl Benzothiophene

Nitrogen-containing heterocycles and sulfur-containing heterocyclic compounds are important intermediates in organic synthesis.Their derivatives have wide application value and prospect in natural products,drug molecules and materials science.Quinoline compounds as an important representative of nitrogen-containing heterocycles,these compounds with anti-inflammatory,anti-tumor,anti-bacterial,analgesic and other characteristics.At the same time,these compounds with good conjugation systems are widely used in materials.Benzothiophene is a commonly used structural unit in pharmacologically active compounds and materials science and has potential application value in many drugs,drug candidates and materials.Therefore,the synthesis of these compounds has been an important area of research for chemists.In this paper,based on the analysis of predecessors,we have developed a new method for the gentle and efficient synthesis of quinoline and benzothiophene.This paper includes the following three parts:Firstly,free-transition-metal catalyzed and transition-metal catalyzed synthesis of quinoline,thiophene and benzothiophene compounds in recent years has been summarized.Secondly,study on the synthesis of 2-arylquinoline and 2-arylbenzoquinoline by C-N/C-C bond construction.Highlights is that the use of cheap aniline and propargyl alcohol as raw materials,aniline to provide nitrogen source,propargyl alcohol ester to provide three carbon sources.The reaction process undergoes intermolecular nucleophilic reaction,followed by an intramolecular electrophilic process,and a "pot method" synthesizes a series of quinoline compounds.Thirdly,study on the synthesis of benzothiophene derivatives by the formation of C-S bonds using copper catalytic system.The reaction was carried out using 3-(o-iodophenyl)-propan-1-one as the raw material,potassium sulfide as the sulfur source,the coupling reaction occurs by potassium sulfide and C-X bond,followed by enol tautomerism,intramolecular cyclization and dehydrogenation aromatization,efficient synthesis of benzothiophene derivatives.