Selective Preparation Of Quinoline/Triazole Derivatives Based On Alkynyl Phosphonates

The 1,2,3-triazole compounds have special biological activity due to the special structure of triazene pentaheterocene,and these compounds have a wide range of applications in pesticides,pharmaceuticals,macromolecules and surface chemistry.The Especially in the pharmaceutical and pesticide,1,2,3-triazole structure as the parent of small molecules in the anti-bacterial,anti-fungal,anti-tuberculosis,anti-cancer and ion channel activator and so has the exact effect;,Some of the heteroatom substituted 1,2,3-triazole compounds can also serve as herbicides,fungicides,pesticides and plant growth regulators,play an important role in agricultural production.In view of the wide application value of 1,2,3-triazole derivatives,the synthesis of these compounds has been widely concerned by synthetic chemical workers.Traditional methods of preparation,such as the Huisgen reaction and Sharpless click chemistry,have made significant contributions to the synthesis of 1,2,3-triazole derivatives.A series of substituents are successfully prepared.-triazole derivatives.However,the authors have found that the use of cyclic addition reactions of intermediate alkynes and azide compounds to produce heteroatom functional groups is less reported for the 1,2,3-triazole derivatives.Therefore,this paper presents a method for synthesizing heteroatom functional group substituted 1,2,3-triazole derivatives.Quinoline compounds have excellent biological activity and pharmacological activity,in the biomedical and pesticide has a very wide range of applications.In the biomedical and pesticide have a wide range of applications.In the pharmaceutical field quinoline compounds have antibacterial,bactericidal,anti-allergy,anti-malarial,anti-tumor,anti-cancer,antihypertensive,antidepressant and enhance the role of memory;quinoline compounds in the pesticide field both sterilization and insecticide The Especially for heteroatom substituted quinoline derivatives,the drug activity has greatly improved.However,the traditional method of synthesizing quinoline compounds requires the use of metal catalysts,the reaction conditions are harsh,and there are few reports on quinoline derivatives with heteroatom substitutions.Therefore,a mild,easy-to-use,It is important to replace the quinoline compound by atom.In this paper,the synthesis of 1,2,3-triazole derivatives and quinoline derivatives with phosphine atoms substituted by phosphine phosphines as substrates was studied.The following studies were carried out:1.First describes the triazole derivatives and quinoline derivatives in the field of medicine and pesticide applications,and phosphorus-containing triazole derivatives and quinoline derivatives of the synthesis method was briefly introduced.Finally,according to a large number of literature surveys and the specific circumstances of the laboratory made the subject.2.We studied the conditions of[3 + 2]cycloaddition reaction under Cu?I?catalyzed by benzyl azide and phosphine phosphine as the substrate study the effects of solvent and temperature on the reaction Impact.The optimum reaction conditions for the synthesis of 1,2,3-triazolylphosphine compounds were obtained by ring addition reaction.Then,under the optimum reaction conditions,we obtained a series of 4-aryl-5-The phosphonate-1,2,3-triazole compound?9a-9e?provides a simple and feasible method for the synthesis of 1,2,3-triazole derivatives substituted by phosphorus atoms.We also tried to synthesize sulfur-substituted quinolines using alkynesulfide and benzyl azide as the substrate,but only the hydrolyzed product?11a-11c?was obtained.3.We used the phosphine phosphine ester and benzyl azide as the substrate to study the effects of acid,solvent,oxidant and temperature on the synthesis of quinoline phosphine ester compounds,and the optimum reaction conditions were determined by using two equivalents of trifluoromethanesulfonic acid as the acid and DCE as the solvent,using air as the oxidant and the reaction temperature at room temperature.And a series of quinophosphonic acid ester compounds?10a-10s?were synthesized at high yield under the optimum conditions.The reaction is simple,mild conditions,high yield,good selectivity.4.We also got the compound 10p single crystal,and its structure was X-ray diffraction analysis.According to the mechanism of[4 + 2]cycloaddition reaction and the structure of the product,the possible mechanism of synthesis of quinoline phosphines is proposed.All the target compounds and intermediates were confirmed by IR,¹H NMR,¹³C NMR,³¹P NMR,MS and HRMS.