DIASTEREOSELECTIVE SYNTHESIS AND STRUCTURE OF SPIROISOXAZOLINE DERIVATIVES

Synthesis of a series of novel spiroisoxazolines has been accomplished in good yields by regio- and diastereoselective 1,3-dipolar cycloaddition of (E)-2-arylidene-(2H)-indanones 1a-d and (E)-2-arylidene-(2H)-3- methylindanones 2a-d to arylnitrile oxides 3e-g. The structure of the spiroadducts was elucidated by 1 H and arylnitrile oxides with some 2-arylmethylene-1,3-indanediones (13) or (Z)-3-arylidene-2(3H)- benzofuranones (14) leads to a single spirocompound. The reaction was regioselective (100%). The structures of the spiroadducts were elucidated by 1 H, 13 C NMR and MS spectral studies. To the best of our knowledge the reaction of (E)-2-arylidene-(2H)-indanones 1a-d and (E)-2-arylidene-(2H)-3- methylindanones 2a-d with arylnitrile oxides 3e-g has not been previously reported.