Synthesis Of Indenamines Derivatives Via Cyclization Of Iminium Ions And Olefins

This paper is divided into two chapters:Part?:?1?A brief description of the application of indane derivatives?2?It summarizes the method for synthesizing indane derivatives:intermolecular ring-closing reactions and intramolecular ring-closing reactionsThe construction of the full carbon ring skeleton is the core problem of synthetic chemistry.The indenamines derivative is a full-carbon ring skeleton that is widely found in many active natural products.And it has important application value in drug molecules,transition metal complexes,functional materials and so on.Therefore,the method of synthesizing indane derivatives is favored by many chemical researchers.In recent years,the synthesis methods of indane derivatives have been extensively studied.The synthesis methods of simple,green and high atomic economy are rarely reported at present,so it is of great significance to synthesize indane derivatives from this point of view.Part ?:Synthesis of Indenamines derivatives by cyclization of imine ions and olefinsIntroducing the Intramolecular cyclization synthesis of N-indenylsulfonamide derivatives and the research ideas of this subject.The experimental part describes the synthesis of N-indenylsulfonamide derivatives by intramolecular cyclization using Alkenyl benzaldehyde and TsNH₂ as substrates under the catalysis of anhydrous ferric chloride.The internal cyclization method of the derivative was carried out,and the conditions of the template reaction were screened to obtain the optimal conditions:anhydrous ferric chloride?20 mol%?,the temperature was 60?,and the solvent was dichloromethane.The yield of the expected product is up to 85%under the conditions.Under the optimal conditions,the universality of substrate was studied,and more than twenty kinds of N-indenylsulfonamid derivatives were synthesized.Various amines were further screened,and the N-indenylsulfonamide is derivatized to the corresponding indanone.Finally,the mechanism of the reaction was studied in detail and it was found that the reaction was an imine ion intermediate process.The product was identified by nuclear magnetic resonance and high resolution mass spectrometry.