A designed method for the preparation of 3-aminomethylated
maleimides
via Morita–Baylis–Hillman (MBH) reaction was developed.
This phosphine-catalyzed coupling adopted maleimides and 1,3,5-triazinanes
as the substrate, giving a series of 3-aminomethylated maleimide derivatives
with a double bond retained on the maleimide ring in 41–90%
yield. Acylation, isomerization, and Michael addition of the obtained
products demonstrated the synthetic application of the present protocol.
The results of control experiments indicated that phosphorus ylide
formation and elimination take place during the reaction pathway.