Efficenct Method For Multicomponent Synthesis Of Tetrahydropyridine Derivatives

Organic catalytic tandem reaction is currently a hot topic in the field of organic synthesis. In the synthesis of complex organic molecules, this approach can at the same time maximize the utilization of raw materials, avoiding the separation of the reaction intermediates, thus reducing the reaction cost. So it is a novel reaction process both economical and environmental- friendly. The synthesis of tetrahydropyridine and its synthetic deriva tives has long been a difficulty and hot spot in synthesis research field. Many researchers have been committed to the synthesis of such compounds. This paper is an attempt to explore the synthetic method of multi- functional tetrahydropyridine and its derivatives. This paper presents several organic catalytic tandem reactions which involve Baylis-Hillman carbonates, and build a series of multi- functional tetrahydropyridine derivatives. Thesis is divided into the following three sections:The first chapter introduces the Baylis-Hillman reaction and its reaction mechanism, as well as a simple kinetic resolution of Baylis-Hillman. Then emphasis is put on the introduction of two important reaction process: the allylic alkylation of Baylis-Hillman carbonates when it is catalyzed by cinchona alkaloid, and the substitution reaction with heteroatoms as nucleophilic center. And finally, there is a simple introduction to the allylic alkylation of Baylis-Hillman carbonates catalyzed by phosphine.The second chapter introduces the application of tetrahydropyridine derivative in industry and medicine; then the reaction synthesis method of tetrahydropyridine and reaction concerning tetrahydropyridine derivatives are highlighted.The third chapter deals with a research of the Synthesis of polyfunctional tetrahydropyridine reaction when Baylis-Hillman carbonate through one-pot method is catalyzed by triethylenediamine. After a failed attempt at the separated reactions of enamines compound and Baylis-Hillman carbonate, We designed a method to get tetrahydropyridine derivatives with Baylis-Hillman carbonate, methyl acetoacetate and methylamine, by means of one-pot method, but the product is a pair of enantiomers. After that, we have tried a variety of isomerization methods and eventually get a single configuration of poly- functional tetrahydropyridine derivatives.This synthesis method uses some cheap, simple substrates and catalysts, and this method is easy to implement the structural diversity of the substrates, with high atom economy and environmental friendly. It provides a convenient and efficient path to the synthesis of multisubstituted 1,2,3,4-tetrahydropyridine derivatives, conforming with the development trend and requirements of green chemistry.