Kinetic and Thermodynamic Control of the Reaction of 5-Amino-11H-isoindolo[2,1-a]quinazoline with N-phenylmaleimide

Levkov, I., Kysil, A., Shilin, S., Voitenko, Z., Yegorova, T. (2024). Kinetic and Thermodynamic Control of the Reaction of 5-Amino-11H-isoindolo[2,1-a]quinazoline with N-phenylmaleimide. French-Ukrainian Journal of Chemistry, 12(1), 157–163. https://doi.org/10.17721/fujcV12I1P157-163

The reaction of 5-amino-11H-isoindolo[2,1-a]quinazolIne with maleimides is not a typical Michael reaction but proceeds through a more complex rearrangement. Depending on the type of control, the reaction with N-phenylmaleimide can follow two different pathways. Probable reaction mechanisms have been proposed for both kinetic and thermodynamic control. The structures of the reaction products were confirmed, in particular, by COSY and HMBC methods.