Catalyst-Free, Three-Component Synthesis of Amidinomaleimides

Maleimide and amidine functionalities often appear in
medicinal
and natural product targets. We describe a catalyst-free, three-component
coupling reaction for the synthesis of amidinomaleimides. This one-pot
reaction fuses a broad range of secondary amines and aldehydes with
azidomaleimides. The conditions are mild, simple, modular, high yielding,
and amenable to aqueous solvents. Most reaction products can be sufficiently
purified without column chromatography. The synthesis creates complex,
multifunctional molecules with four different molecules, including
a tripeptide, arrayed around an amidinomaleimide core.