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.

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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
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article

Serendipitous Two Successive Rearrangements of Ugi Adducts Promoted by a Base and a Copper Catalyst

Parviz Rashidi Ranjbar, Reihane Peirow, Behrouz Notash, Yasin Mohamadkhani et al.
The Journal of Organic Chemistry
Multicomponent Synthesis of Heterocycles
article

Serendipitous Two Successive Rearrangements of Ugi Adducts Promoted by a Base and a Copper Catalyst

Parviz Rashidi Ranjbar, Reihane Peirow, Behrouz Notash, Yasin Mohamadkhani, Mohammad Mahdavi
article en

Abstract

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.

The Journal of Organic ChemistryVol. 91(6)
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)
Openalex Percentile: Top 73%
Multicomponent Synthesis of Heterocycles
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