Iodine Reagent-catalyzed Synthesis Of ?-substituted-2H-azirines

With unique structure and function,heterocyclic compounds play agreat role in the field of organic and medicinal chemistry.Finding new methods for synthesizing heterocyclic compounds that is known and synthesizing new heterocyclic compounds are important research contents in organic synthetic chemistry.Amongthe various heterocyclic compounds,nitrogen heterocyclic compounds aregiven more attention because of good biological activity and medicinal value.As the smallest nitrogen-containing heterocyclic compound,2H-azirines is also a kind of important compound found in several natural products and it can be used as intermediate which can be synthesized into a variety of other active compounds.However,due to its special structure,the synthesizing methods of 2H-azirines is limited.Therefore,there are few researches on the synthesis of these compounds at home and abroad,let alone the synthesis of 2H-azirines by enamidone and iodine reagent.The researches in the paper are as follows:1.The synthesis method and application of ?-substituted-2H-azirines under iodine reagent-mediated conditions are researched.Through the screening inexperiment,the proper reaction system of KI/TBHP is found and the synthesis of 2Hazirines is realized by usingenamine as raw material.22 new kinds of 2H-azirines compounds are synthesized.A new method for the formation of 2H-azirines compounds by cross-oxidative coupling of different ketenones and fatty acids is found.2.Using iodine as mediate,the substitution reaction of ?-position of 2H-azirines is studied.The reaction conditions of KI as accelerators are screened by experiments and the interchange of 2H-azirines ?-acyloxygroups is realized.A total of 20 new 2Hazirines alpha-acyloxy compounds are synthesized.For the first time an example of nucleophilic substitution between lipid and carboxylic acid under metal-free reaction conditions is found.The reaction system has advantages including: easy-to-obtain raw materials,no metal contained,economical and environmental-friendly and widelyapplied.3.The NMR and HRMS of the synthesized 2H-azirines compounds and 2Hazirines ?-acyloxy compounds are characterized.