Construction And Study Of Novel Small Organic Fluorescent Molecules And Primary Exploration Of Heter-Pauson-Khand Reaction Based On Isocyanide

Because of the simple structure, less cost, and highly efficient, the design and development of novel small organic fluorescent molecules become more and more important compared with large molecules and polymer fluorescence. There is a need for facile, efficient, and nonpolluting synthetic procedures that reduce the use of organic solvents and toxic reagents.Isocyanides have an almost unique set of properties with CO because of the carbene structure of their carbon atom, so that some chemical properties are similar to CO but itself also has many advantages that the diversities of reaction, for example they can react with both nucleophiles and electrophiles on the same carbon atom, and the products exist futher modified imine structure. Isocyanide-based Multicomponent reactions have emerged as a powerful strategy for the synthesis of chemically, biologically and potential application value important organic molecules. This protocol allows molecular complexity approaches the concept of an ideal synthesis.In the first chapter, we generally described the isocyanide as highly reactive intermediate and its extensive applications of reaction types in organic synthesis. Then we generally reviewed the applications and the advances of isocyanide in Hetero-Pauson-Khand type reaction. Particularly, we explored the possibility of Pauson-Khand-type reaction with the Isocyanide instead of CO.In the second chapter, we design and develop a synthetic methodology based on IMCRs to construct pyrrole-2,5-dione and 5-imino-pyrrol-2(5H)-one small organic fluorescent molecules via a one-pot reaction under isocyanide, aromatic aldehyde and cyano acetamide by suitable regulation The optimized conditions for this reaction are as follows:1 equiv additive of I2, 0.5 equiv base of DABCO, and DMSO/HFIP as the solvent at 100℃ under 4-6 h.We obtain two organic fluorescent products, by adding molecular sieve or acid to regular the hydrolysis process.In the third chapter, we test the one kind of new type of fluorescent nuclear by UV and FL, and explore the potential application value of the fluorescence properties preliminary.In chapter four, a novel Co(Ⅱ)-catalyzed intermolecular Herer-Pauson-Khand-type reaction of isocyanide with acetylene-isothiocyanates substrates to afford N-cyclohexyl-3-phenyl-2H-thieno[2,3-b]indol-2-imine compound is explored primary. In addition, Heter-Pauson-Khand-type reaction based on isocyanides has some advantages, such as bw toxicity, the product containing particular group etc.