What question did this study set out to answer?

The aim is to explore the reactions of 3-oxobutanamides with β-enaminones and primary amines using a Mn redox system.

June 23, 2026Open Access

Reaction of 3-Oxobutanamides with β-Enaminones and Primary Amines Using Mn(III)/Mn(II) Redox System. A New Approach to Highly-Substituted 3-Oxo-2,3-dihydro-1H-pyrrole-2-carboxamides

Key Points

The aim is to explore the reactions of 3-oxobutanamides with β-enaminones and primary amines using a Mn redox system.
Reactions conducted using Mn(OAc)3•2H2O under oxygen atmosphere.
Products obtained were characterized as 2,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrrole derivatives.
Product yields were reported for 27 and 28 examples in respective reactions.
The reaction with β-enaminones resulted in excellent yields of pyrrole-2-carboxamides.
The reaction with primary amines yielded pyrrole-2,4-dicarboxamides in quantitative yields.
A proposed mechanism involves Mn(III) catalytic action and a pinacol-type rearrangement.

Abstract

The reaction of N -aryl-3-oxobutanamides with β -enaminones in the presence of a catalytic or substoichiometric amount of Mn(OAc) 3 •2H 2 O under an oxygen atmosphere afforded the corresponding 2,5-dimethyl-3-oxo-2,3-dihydro-1 H -pyrrole-2-carboxamides in excellent yields (27 examples). In contrast, the reactions with various primary amines cleanly afforded the corresponding 2,5-dimethyl-3-oxo-2,3-dihydro-1 H -pyrrole-2,4-dicarboxamides in quantitative yields (28 examples). A plausible mechanism for product formation, including the role of Mn(III) as a catalyst and a pinacol-type 1,2-methyl rearrangement, is proposed.

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