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Chemoselective synthesis of multisubstituted pyrrolo[3,4-b]pyridine-2,5,7(6H)-trione through a cascade reaction

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Abstract

A simple and efficient protocol for direct synthesis of multisubstituted 6-alkyl-4-chromenyl-1-aryl-3,4-dihydro-1H-pyrrolo[3,4-b]pyridine-2,5,7(6H)-trione derivatives is presented by a cascade reaction of 3-formylchromones, Meldrum’s acid and α-aminomaleimides as readily accessible starting materials. In this chemoselective, metal catalyst-free approach Michael addition/intramolecular cyclization and elimination of acetone and carbon dioxide occur consecutively. The significant advantages of this strategy are creating a C–N and a C–C bond, short reaction times, excellent yields (68–80%), and a metal-free catalyst.

Graphical Abstract

A simple and efficient protocol for direct synthesis of multisubstituted 6-alkyl-4-chromenyl-1-aryl-3,4-dihydro-1H-pyrrolo[3,4-b]pyridine-2,5,7(6H)-trione derivatives is presented by a cascade reaction of 3-formylchromones, Meldrum’s acid and α-aminomaleimides as readily accessible starting materials.

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Fig. 1
Scheme 1
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Acknowledgements

We gratefully acknowledge the support of this work by the Tarbiat Modares University Research Council.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

    Abdolali Alizadeh & Reihaneh Moterassed

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  1. Abdolali Alizadeh
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  2. Reihaneh Moterassed
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Correspondence to Abdolali Alizadeh.

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Alizadeh, A., Moterassed, R. Chemoselective synthesis of multisubstituted pyrrolo[3,4-b]pyridine-2,5,7(6H)-trione through a cascade reaction. J IRAN CHEM SOC (2024). https://doi.org/10.1007/s13738-024-03023-9

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