Issue 2, 2024

Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts

Abstract

Two tandem catalytic systems are described for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts as starting materials. 4-Aryl-3-pyrrolyl- and 4-aryl-3-indolyl-maleimides were successfully obtained via a Pd(OAc)2/PPh3 based protocol. In contrast, maleimide-fused pyrrolo and indolo[1,2-a]quinolines were obtained in a complementary methodology using CuI/L-proline. These strategies involved a combination of benzylic amine oxidation, trans-amidation, intramolecular Knoevenagel condensation, and N-arylation reactions. Computational investigations provide further insights into this reaction sequence.

Graphical abstract: Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts

Supplementary files

Article information

Article type
Paper
Submitted
06 Oct 2023
Accepted
30 Nov 2023
First published
05 Dec 2023

Org. Biomol. Chem., 2024,22, 380-387

Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts

F. Bandehali-Naeini, Z. Tanbakouchian, N. Farajinia-Lehi, N. Mayer, M. Shiri and M. Breugst, Org. Biomol. Chem., 2024, 22, 380 DOI: 10.1039/D3OB01620J

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