© 2015 Pleiades Publishing, Ltd.1,3-Dipolar cycloaddition of stable N,N′- and C,N-cyclic azomethine imines based respectively on pyrazolidin-3-one and 3,4-dihydroisoquinoline to N-arylitaconimides proceeds strictly regioselectively resulting in spiro-joint heterocycles in good yields. The regioselectivity of the addition of N,N′-cyclic azomethine imines is reversed with respect to that of C,N-cyclic azomethine imines. The diastereoselectivity of the cycloaddition depends apparently on the substituents at the central nitrogen atom in the azomethine imine fragment.
Koptelov, Y. B., Molchanov, A. P., & Kostikov, R. R. (2015). Regio- and diastereoselective cycloaddition of stable cyclic azomethine imines to N-arylitaconimides. Russian Journal of Organic Chemistry, (8), 1134-1143. https://doi.org/10.1134/S1070428015080126