The Study Of The Application Of Ionic Liquids And The Synthesis Of Tryptophol And Propargyl Ester Compounds

With the emergence of the concepts of “green chemistry” and “atom economy”, forming a new C-C bond via transition-metal-catalyzed the activation of inactive C-H bond has been a hot research field. The C-C bond formation through C-H bond oxidative cross-coupling approach has great advantages, for it avoids the using of expensive metal catalysts in this process. Cross-dehydrogenative coupling(CDC) reaction is one of the typical representatives. Nowadays, metal-free catalyzed CDC reaction has been the new hotspot. However, study of using classical ionic liquids which contained heterocyclic structure as promoters or catalysts in the CDC reaction has not been reported. Based on this, we launched our research work.Firstly, based on our research in the synthesis and application of ionic liquids, a series of simple structure of the ionic liquid containing bromine negative ions were synthesized, and their structures had been characterized.Then, 5-(aryloxy)-1H-pyrazole-4-carbaldehydes were regarded as substrates, IL-promoted intramolecular CDC reaction chromeno[2,3-c]pyrazol-4(1H)-one formation conditions were optimized. We concluded that 1,3-dibutyl-1H-benzo[d]-[1,2,3]triazol-3-ium bromide was the optimum promoter which consumption was 0.5 equiv; tert-butyl hydroperoxide(TBHP) was the best oxidant which consumption was 0.2 mL; H2 O was the excellent solvent which consumption was 0.1 mL; and the reaction mixture was stirred at 90 oC for 24 h was the optimum condition. Then, the scope of the reaction was investigated. Substrates bearing either electron-withdrawing groups or electron-donating groups all led to the annulation products in moderate to good yields. Gram-scale oxidative coupling reaction was investigated, and the yield of product was considerable with mode reaction. The circulation use of the ionic liquid was also inspected which could be utilized repeatedly five times without any loss of activity. Finally, controlled experiments were carried out. We concluded that this reaction may be a radical reaction.3,4-Dihydropyrimidin-2(1H)-(thio)ones compounds which have important pharmacological activity have wide application in the field of anti-microbial, anti-virus, anti-tumor, anti-bactericidal and inflammatory, so its green method of synthesis has aroused widespread concern. The Biginelli Reaction which catalyst is ionic liquid with imidazolium cation and p-toluenesulfonic acid anion, solvent is ethanol is be studied under reflux condition for 1.5 h in this paper. 3,4-Dihydropyrimidin-2(1H)-(thio)ones compounds are be synthesized.The skeleton of Pyrroloindoline and Furoindoline with indole ring are widely present in natural products. They have very important physiological activity and medicinal value. Copper-catalyzed intermolecular asymmetric propargylic dearomatization of indoles build these compounds. This paper synthesize precursor compound of these compounds-tryptophol and propargyl ester.