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Updated: Jun 4, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Knoevenagel condensation of 4,5- and 1,8-diazafluorenes
Darya S Cheshkina1, Christina S Becker1, Alina A Sonina1
1N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentieva 9, 630090 Novosibirsk, Russia.
Abstract:
Diazafluorenylidenes are potential antitumor agents, ligands, and functional materials. However, there are currently only limited methods for their synthesis, which are complicated and typically based on modifications of 4,5-diazafluorenone. Herein, we systematically studied the Knoevenagel condensation of both 4,5- and 1,8-diazafluorenes with aromatic aldehydes and evaluated the diazafluorenes' nature and solvent influence on the mechanism and reactivity. We also identified conditions allowing the preparation of both 4,5- and 1,8-diazafluorenylidenes in yields up to 85% minimizing complicated synthetic or experimental workup procedures. Additionally, the condensation of diazafluorenes with ketones resulted in unique di(pyridin-2-yl)methylene)-9H-diazafluorenes being electron-deficient ligands and functional materials.
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