Cycloaddition of synthetic equivalent of non-stabilized aminonitrile ylides: A new route to amino-substituted delta(2)-imidazolines and delta(3)-1,2,4-triazolines

The N-unsubstituted nonstabilized azomethine ylides generated from the desi lylation of N- [(trimethylsilyl)methyl]iminium triflates undergo successful cycloaddition to strongly polarized sulfonylimines and diethyl azodicarbox ylate to produce the corresponding Delta (2)-imidazolines and Delta (3)-1,2 ,4-triazolines together with the initial cycloadducts. The initial cycloadd ucts are converted to the corresponding aminonitrile ylide cycloadducts. Th us the present process provides a new route to amino-substituted Delta (2)- imidazolines and Delta (3)-1,2,4-triazolines that are otherwise relatively inaccessible.