Direct Synthesis Of Spirocyclic Bitetrahydroquinolines And Functionalized 1,2-Dihydroquinolines By Step-Controlled Povarov-Type Reaction

The heterocyclic spiro compounds presented in many bioactive natural products and synthetic drugs which are important structural units of these substances.It also has made a great contribution to empolder new green pesticides with environmentally friendly and excellent insect-resistant,good antibacterial properties.As a consequence,this structure has attracted the attention of both medicinal chemists and synthetic chemists for its potential as an importantpharmacophore.However,to the best of our knowledge,the existing methods for obtaining such compounds are tedious,with long synthetic approaches and low yields.The nitrogen-containing heterocyclic compounds have become a hotspot in the current drug synthesis and development design.As their unique biological activity,good internal adsorption and low toxicity.Tetrahydroquinoline compounds are a series of common nitrogen heterocyclic compounds,which have a wide range of biological activity,and have a great effect in theprevention and treatment of atherosclerosis,hyperlipidemia and arrhythmia and other common diseases.Moreover it can be used as the organic synthesis of the ligand and the intermediates to synthetic colourant.As the compounds are widely used,investigation and development more synthesis methods of such compounds are necessary.In this paper,1,2-dihydroquinoline compounds and aromatic imines were used as raw materials to direct synthesis of spirocyclic bi-tetrahydroquinolines with spirocyclic and tetrahydroquinoline skeleton by a novel povarov-type reaction.Add up to 15 aldimine substrates and 8 1,2-dihydroquinoline substrates were synthesized and 23 novel compounds with spirocyclic bi-tetrahydroquinolines were synthesized.Meanwhile we put forward a reasonable reaction mechanism.Then,by changing the reaction conditions,the reaction can selectively retain in the first stage of the Povarov reaction,and functionalized 1,2-dihydroquinoline can be efficiently synthesized.8 aldimines substrates and 4 1,2-dihydroquinoline substrates were synthesized,and 12 functionalized 1,2-dihydroquinoline compounds were synthesized which are new compounds.In this thesis we have succeeded in developing an efficient strategy for straightforward synthesis of novel spiro bitetrahydroquinolines.This represents a brand-new Povarov-type reaction which could selectively controlled step by step.The spirocyclic bi-tetrahydroquinoline compounds or the functionalized 1,2-dihydroquinoline compounds can be selectively produced with different reaction conditions.