Research On 1,3-dipolar Cycloaddition Reaction Based On The Participation Of Nitrile Oxide

In this paper,there different series of heterocycles bearing potential bioactivities were synthesized by using newly designed cycloaddition reactions of nitrile oxide generated in situ from acetophenone and tert-butyl nitrite.The research contents were classified into the following two parts??.Construction of pyrrolo[3,4-d]isoxazolines via [3+2] cycloaddition of Nitrile oxide with maleimide.Firstly,we used model reaction of acetophenone and tert-butyl nitrite and maleimide to optimizethe reaction conditions by screening solvents,temperature and the ratio of the reactants.Then,with the optimized reaction conditions in hand,we extended the reaction scope of the [3+2] cycloadditions by diversifying ketone and maleimide,and obtained 30 pyrrolo[3,4-d]isoxazolines in the highest yield of 87%.the chemical structure of target products was unambiguously determined by singlecrystal X-ray analysis.The reaction mechanism was suggested.II.Constructionofoxathiolo[3,4-d]isoxazole and tetrahydrophospholo[2,3-d]isoxazole4-oxidevia[3+2]cycloadditionof nitrile oxide with sultone and 3-methyl-1-phenyl-2-phospholene-1-oxide.We used model reaction of acetophenone and tert-butyl nitrite with sultone and 3-methyl-1-phenyl-2-phospholene-1-oxide to optimize the reaction conditions by screening solvents,temperature and the ratio of the reactants.Then,with the optimized reaction conditions in hand,Under the optimal reaction system,12 potentially biologically active oxathio products were synthesized,and the reaction mechanism was suggested.