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  • Thermal 1,3-dipolar cycload...
    Yang, Zhi-Wei; Wang, Jing-Fang; Peng, Li-Jie; You, Xiao-Lin; Cui, Hai-Lei

    Tetrahedron letters, 11/2016, Letnik: 57, Številka: 47
    Journal Article

    Display omitted •A metal and catalyst free 1,3-dipolar cycloaddition has been developed.•Gram-scale reaction could be achieved.•Fully substituted pyrazole can be obtained by easy transformation. A metal and catalyst free 1,3-dipolar cycloaddition reaction of azomethine imines with internal alkynes has been developed. Various N,N-bicyclic pyrazolidinones could be prepared quickly under microwave irradiation in moderate to excellent yields (up to 96%). A wide range of azomethine imines and electron-deficient internal alkynes were applicable to this reaction. In addition, gram-scale reaction could be achieved and fully substituted pyrazole can be obtained by easy transformation of N,N-bicyclic pyrazolidinone. This environment friendly dipolar cycloaddition is remarkable for its simplicity in conditions and wide structural diversity.