Synthesis fo di- and cis-triaryl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles and their ring-opening reactiosn

摘要

The #DELTA#~3-imidazoline 3-oxides 1 undergo diastereoselective cycloaddition with dimethyl acetylenedicarboxylate 2 to give 3a,4,5,6-etrahydroimidazo[1,5-b]isoxazoles 3.Termally and base induced ring-opening reactions of compounds 3 were demonstrated.cis-6-Phenyl substituted adducts 3d,e undergo ring opening with secondary but not with tertiary amines.The same adducts undergo regio-and diastereoselective Michael addition with sodium methoxide to give 2-methoxy-3a,5,6-triphenyl-hexahydro-imidazo[1,5-b]isoxazole-2,3-dicarboxylic acid dimethyl esters6.