Jump to main content
Jump to site search


Copper-catalyzed oxidative cleavage of Passerini and Ugi adducts in basic medium yielding α-ketoamides

Abstract

The aerobic oxidative cleavage of Passerini and Ugi adducts in presence of base and copper(I) iodide is studied in detail. The oxidative cleavage yields α-ketoamide along with acid and amide from Passerini and Ugi adducts respectively. Mechanistic investigations revealed that the reaction proceeds via a radical pathway involving molecular oxygen. Control experiments with 18O-labelled Passerini adducts confirmed that the molecular oxygen is the source of oxygen in α-ketoamide. A variety of Passerini and Ugi adducts were studied to explore the effect of substitution. Overall, the present study provides an insight into the reactivity of Passerini and Ugi adducts in strong basic conditions along with a method to prepare α-ketoamides.

Back to tab navigation

Supplementary files

Publication details

The article was received on 08 Jul 2019, accepted on 05 Aug 2019 and first published on 09 Aug 2019


Article type: Paper
DOI: 10.1039/C9NJ03533H
New J. Chem., 2019, Accepted Manuscript

  •   Request permissions

    Copper-catalyzed oxidative cleavage of Passerini and Ugi adducts in basic medium yielding α-ketoamides

    A. Ghoshal, M. Ambule, R. Sravanthi, M. Taneja and A. K. Srivastava, New J. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9NJ03533H

Search articles by author

Spotlight

Advertisements