The Study Of The Multicomponent Tandem Reaction Assisted By β-enamino Ester

The multicomponent tandem reaction is a green chemical synthesis method, which has significant academic values and practical applications. Thesedays multicomponent tandem reaction has become the forefront of hot research topics in synthetic organic chemistry. As one of the active reaction intermediates,β-enaminone and β-enamine esters could be used as the key reaction components for the design of multi-component tandem reactions and development of new efficient synthetic methods for the heterocyclic compounds, thus emerged as a content-rich, practical and innovative research topics. As part of our current studies on investigation of the versatile reactivity of electron-deficient alkynes and the design of new routes for the preparation of biologically active heterocyclic compounds, In this thesis we carried out a series of p-enamine esters assisted multicomponent tandem reactions, and successfully synthesized a series of nitrogen-containing heterocyclic compounds suhc as,2-hydroxydihydropyridines,1,4-dihydropyridines,3-hydroxy-2-pyrrolidinones. and spiro[indoline-3,5’-pyrroline] compounds.1. The practical synthetic procedures for the preparation of the functionalized2-hydroxydihydropyridines.1,4-dihydropyridines, and2-pyrrolidinones was developed through the one-pot three-component reactions of aromatic aldehydes, arylamines. and acetylenedicarboxylates under different reaction conditions. Totally thirty-nine new compounds were prepared and characterized by NMR. IR, LC-MS spectroscopy and single crystal structure of five new heterocyclic compounds were confirmed by X-ray diffraction.2. A practical and efficient procedure for the preparation of the polysubstituted dihydroprydines ande dihydropyridinones derivatives were developed through the four-component reactions of aromatic aldehydes, arylamines, acetylenedicarboxylate. and two active methylene compounds with triethylamine as base catalyst. This four-component reaction is atom efficient, high-yielding and applicable to a wide variety of four reaction components. Sixteen new compounds were fully characterized by spectroscopic methods and confirmed by single-crystal X-ray diffraction of four compounds.3. Synthesis of the functional ized spiro[indoline-3,5’-pyrroline]-2,2’-diones via three-component reactions of arylamines, acetylenedicarboxylates and isatins. Totally twenty new compounds were prepared and characterized by NMR, IR, LC-MS spectroscopy and single crystal structures of two compounds were confirmed by X-ray diffraction.