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Abstract <p>An effective, eco-friendly method was developed for the synthesis of carboxystyryl derivatives of 1,10-phenanthroline, 2,2′-bipyridine, and pyridine via a catalyst- and solvent-free condensation reaction of 4-carboxybenzaldehyde with 2,9-dimethyl-1,10-phenanthroline, 6-methyl-2,2′-bipyridine, 6,6′-dimethyl-2,2′-bipyridine, 4,4′-dimethyl-2,2′-bipyridine, or 2-methylpyridine. For dimethylbipyridines, monosubstituted products were primarily formed, whereas for dimethylphenanthroline, a bis-product was obtained. The formation of a hydrogen bond between the nitrogen atom of the heterocycle and the carboxylic proton of 4-carboxybenzaldehyde enhances the reactivity of the methyl group in the heterocycle.</p>

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An Effective Method for the Synthesis of Carboxystyryl Derivatives of 1,10-Phenanthroline, 2,2′-Bipyridine, and Pyridine

  • 期刊论文

  • 发表日期：

    2026年2月9日

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  • Tatiana N. Gavrishova,
  • Aleksander V. Petin,
  • Alexey V. Shastin,
  • Mikhail F. Budyka

摘要

Abstract

An effective, eco-friendly method was developed for the synthesis of carboxystyryl derivatives of 1,10-phenanthroline, 2,2′-bipyridine, and pyridine via a catalyst- and solvent-free condensation reaction of 4-carboxybenzaldehyde with 2,9-dimethyl-1,10-phenanthroline, 6-methyl-2,2′-bipyridine, 6,6′-dimethyl-2,2′-bipyridine, 4,4′-dimethyl-2,2′-bipyridine, or 2-methylpyridine. For dimethylbipyridines, monosubstituted products were primarily formed, whereas for dimethylphenanthroline, a bis-product was obtained. The formation of a hydrogen bond between the nitrogen atom of the heterocycle and the carboxylic proton of 4-carboxybenzaldehyde enhances the reactivity of the methyl group in the heterocycle.