Studies On The Application Of Sulfonyl Azide In Organic Synthesis

This thesis studied mainly on the Cu(I) catalyzed multicomponent reactions in the presence of terminal alkynes and sulfonyl azides. The whole thesis consists of three parts.:Part I: The recent progress of sulfonyl azide in organic synthesisIn this part, the fundamental characteristics of sulfonyl azide chemistry and current developments are summarized. The focus was placed on decomposition reaction, reduction reaction, cycloaddition reaction of sulfonyl azide, and reactions of sulfonyl azide with nucleophiles. Some reaction rules of sulfonyl azide was reviewed. Furthermore, several new methods to introduce sulfonyl group into orgnic molecules were also introduced.Part II Synthesis of highly substituted 2-imidazolines through a three-component coupling reactionA two-step sequence for the synthesis of 2-imidazolines via CuI catalyzed multicomponent reactions was developed. The process has several advantages including, (1) simple and easily available starting materials (2) special, highly substituted product structure and providing a wide range of aryl and alkyl 2-imidazolines, and (3) high regioselectivity and mild reaction conditions. The related transformations and the application of this method to the preparation of chiral 2-imidazolines containing natural products will be interesting.Part III Microwave-assisted michael addition reaction of indole toα,β- unsaturated compounds under solvent-free and lewis acid catalytic condition3-Substituted indoles are important building blocks for the synthesis of biologically active compounds and natural products We proposed a rapid and efficient method for Michael addition of indole toα,β-unsaturated compounds catalayzed by SnCl₂/Al₂O₃ under microwave irradiation. The significance of our findings relates to reducing the use of organic solvents as potentially toxic and hazardous materials, as well as its simplicity and mild conditions, and inherent lower costs, with more likely industrial applications.