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.
Authors
- Gregory A. Weiss (ORCID: https://orcid.org/0000-0003-0296-9846)
- Wyatt R. Swift‐Ramirez (ORCID: https://orcid.org/0009-0006-3166-8224)
- Lindsay A. Whalen (ORCID: https://orcid.org/0009-0001-1925-7362)
- Kaylee E. Shoemaker (ORCID: https://orcid.org/0009-0006-2893-662X)
- Lia K. Thompson
- Aris V. Rubio
Institutions
- University of California, Irvine (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-23
- DOI
- https://doi.org/10.1021/acs.joc.4c01485
- Citations
- 3
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.70
Funders
- U.S. Department of Energy
- National Institutes of Health
- Advanced Research Projects Agency - Energy
- University of California, Irvine
- Advanced Research Projects Agency
- National Cancer Institute
- Chao Family Comprehensive Cancer Center