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Peer-reviewedCC BYMolecules (Basel, Switzerland)

Triethanolamine-Catalyzed One-Pot Three-Component Domino Annulation Leading to 4H-Pyrano[3,2-c]coumarins: Catalyst Reusability and Decagram-Scale Synthesis

  • Essam M. Eliwa1
  • Atheer A. Mahmood2
  • Rania S. Ali3
  • Marwa ElS. Ahmed4
  • Abdullah A. Ahmed1
  • Ewies F. Ewies5
  • Roman Dembinski6,7
7 affiliations
  1. 1Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City 11884, Cairo, Egypt
  2. 2Department of Chemistry and Biochemistry, College of Medicine, Al-Iraqia University, Baghdad 7366, Iraq
  3. 3Department of Basic Science, Faculty of Technology and Education, Capital University, Cairo 11281, Egypt
  4. 4Chemistry Department, Faculty of Women for Art, Science and Education, Ain Shams University, Heliopolis 11757, Cairo, Egypt
  5. 5Organometallic and Organometalloid Chemistry Department, National Research Centre, 33 ElBohouth St., (Former El Tahrir) Dokki, Giza 12622, Egypt
  6. 6Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland
  7. 7Department of Chemistry, Oakland University, 146 Library Dr., Rochester, MI 48309-4479, USA
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Abstract

A triethanolamine (TEOA)-catalyzed, one-pot, three-component reaction of 4-hydroxycoumarin, aldehydes, and malononitrile was developed as a highly atom-economic domino protocol for the synthesis of biologically significant 4H-pyrano[3,2-c]coumarins. This cascade sequence proceeds through the successive formation of three new σ bonds (two C—C and one C—O). The protocol exhibited a broad substrate scope and proceeded rapidly and efficiently in methanol at ambient temperature or in water at 85 °C. 4H-Pyrano[3,2-c]coumarins were isolated in 51–95% yields using a simple workup without column chromatography. Sustained TEOA catalytic activity across seven consecutive cycles was demonstrated. Gram- and decagram-scale protocols were elaborated, and the plausible mechanistic pathway was proposed in this study.

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Cite

BibTeXRIS
BibTeX
@article{eliwa2026triethanolaminecatalyzed,
  title = {{Triethanolamine-Catalyzed One-Pot Three-Component Domino Annulation Leading to 4H-Pyrano[3,2-c]coumarins: Catalyst Reusability and Decagram-Scale Synthesis}},
  author = {Essam M. Eliwa and Atheer A. Mahmood and Rania S. Ali and Marwa ElS. Ahmed and Abdullah A. Ahmed and Ewies F. Ewies and Roman Dembinski},
  journal = {Molecules (Basel, Switzerland)},
  year = {2026},
  month = oct,
  doi = {10.3390/molecules31193541},
  url = {https://europepmc.org/article/PMC/PMC13667214},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Triethanolamine-Catalyzed One-Pot Three-Component Domino Annulation Leading to 4H-Pyrano[3,2-c]coumarins: Catalyst Reusability and Decagram-Scale Synthesis
AU  - Essam M. Eliwa
AU  - Atheer A. Mahmood
AU  - Rania S. Ali
AU  - Marwa ElS. Ahmed
AU  - Abdullah A. Ahmed
AU  - Ewies F. Ewies
AU  - Roman Dembinski
PY  - 2026
DA  - 2026/10/01
JO  - Molecules (Basel, Switzerland)
DO  - 10.3390/molecules31193541
UR  - https://europepmc.org/article/PMC/PMC13667214
AB  - A triethanolamine (TEOA)-catalyzed, one-pot, three-component reaction of 4-hydroxycoumarin, aldehydes, and malononitrile was developed as a highly atom-economic domino protocol for the synthesis of biologically significant 4H-pyrano[3,2-c]coumarins. This cascade sequence proceeds through the successive formation of three new σ bonds (two C—C and one C—O). The protocol exhibited a broad substrate scope and proceeded rapidly and efficiently in methanol at ambient temperature or in water at 85 °C. 4H-Pyrano[3,2-c]coumarins were isolated in 51–95% yields using a simple workup without column chromatography. Sustained TEOA catalytic activity across seven consecutive cycles was demonstrated. Gram- and decagram-scale protocols were elaborated, and the plausible mechanistic pathway was proposed in this study.
SN  - 1420-3049
ER  -