Study On The Synthesis And Characterization Of The Polysubstituted 3-(Isoxazol-5-yl)pyrroles And Indole [3,2-b] Carbazole Derivatives

Pyrrole and its multisubstituted derivative is a kind of important five-membered hetercycles,which individually or as a core framework exists in a lot of product structure,and some of them has good bioactivities,such as anti-inflammatory,antibacterial,antiviral,EP1 receptor antagonist,stability and antispasmodic,anticancer activity etc.Indole [3,2-b] carbazole derivatives have a structure similar to the pentacene,a large π conjugated system and a rigid plane characteristic,which can be chemically modified in multiple sites.Therefore,they have very good biological activities and photoelectric properties,playing an important role in the field of pharmaceutical and materials.Isocyanide,as an important organic building blocks,is widely aplaying in the synthesis of nitrogen heterocyclic compounds,some bioactive molecules,and natural products.Our team,for many years,has been committed to the use of structure and reaction characteristics of different isocyanides to design and explore new reaction types,aiming at building a diversity of heterocyclic compounds.In this study,based on the cycloaddition reactions and selecting p-Tosylmethyl isocyanide(TosMIC)and adjacent alkenyl aromatic isocyanide as the breakthrough point,we have synthesised a series of polysubstituted 3-(Isoxazol-5-yl)pyrroles and indole [3,2-b] carbazole derivatives separately,which enrichs the synthesis methods of these compounds and lays the synthetic foundation for its application research.My study mainly includes the following two parts:1.Built a series of Polysubstituted 3-(Isoxazol-5-yl)pyrroles by the intermolecular [3+2] cycloaddition of TosMIC and styrylisoxazoles.The reaction has many advantages,such as easy accessibility of the starting materials,mild conditions,good to excellent yields and good compatibility of different functional groups,which expands and enrichs the multisubstituted pyrrole derivatives synthesis methods based on isocyanide as a raw material.2.Built a series of Indole [3,2-b] carbazole derivatives by the intermolecular [4 + 1)/intramolecular [4+2] cycloaddition of adjacent alkenyl aromatic isocyanide and alkylidene indole ketones.The reaction has many advantages,such as easy accessibility of the starting materials,the structure of the product is easy to control by adjusting the raw materials,,which provides a new method and a train of thought for the synthesis of Indole [3,2-b] carbazole derivatives.