A Synthesis Of Isoxazolines Featuring An Azido Substituent In Copper-Catalyzed Oxyazidation Of Unactivated Alkenes

Heterocyclic compound plays an important role in both pharmaceutical activity and organic synthesis, for which is closely related with N, O and S actoms. For now, chemists are focussed on studying spiro, azole and bicyclic compounds which are unique activated moleculars in medicine. For example,90% of pesticide are heterocycles, especially N-heterocycles, and their research, extention and application are typical cases in pesticide and drug. In few decades, some biologists would like to shed light on N-heterocycles’ application on biology and physiology such as COX-2 inhibitor and photoaffinity labeling agent for biomolecule. N-heterocycles exhibit various activities in chemistry, medicine, biology and agriculture. In that case, numerous of synthesis methods have been reported in some decades. Millions of N-heterocycles and their derivates have been produced by metal-catalyzed reactions, microwave reactions, radical reactions and initial huisgen 1,3-dipolar cycloadditions. In this paper, two routes were proposed to obtain novel isoxazolines featuring an azido substituent, which have the merit of cheap and rapid, respectively. Both of the methods were easy to operate, no by-product, toleranted well and afforded two efficent pathways to gain isoxazolines. Afterward, we got an isoxazoline bearing a 1, 2,3-triazole with product of phenylacetylene through "click" chemistry. To our surprise, the addition of activated structure led to increase compound’s bioactivity dramatically.