Serendipitous Two Successive Rearrangements of Ugi Adducts Promoted by a Base and a Copper Catalyst
A unique two-step, base-promoted rearrangement of post-Ugi products under copper catalysis is presented. Mechanistic studies revealed that the rearrangement proceeds via sequential amidation, with the copper(I) catalyst facilitating the reaction through carbonyl coordination. This work not only introduces a new synthetic route for the construction of conjugated imines but also provides valuable insights into the mechanistic pathways of post-Ugi rearrangements, paving the way for further exploration of intermolecular reactions and broader synthetic applications.
Authors
- Parviz Rashidi Ranjbar (ORCID: https://orcid.org/0000-0001-8917-5330)
- Reihane Peirow
- Behrouz Notash
- Yasin Mohamadkhani
- Mohammad Mahdavi
Institutions
- University of Tehran (IR)
- Max Planck Institute for Metabolism Research (DE)
- Endocrinology and Metabolism Clinical Sciences Institute
- Shahid Beheshti University (IR)
- Tehran University of Medical Sciences (IR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-01-29
- DOI
- https://doi.org/10.1021/acs.joc.5c01595
- Primary Topic
- Multicomponent Synthesis of Heterocycles
- Type
- article
- Field-Weighted Citation Impact
- 0.00