Synthesis of phenyl- and pyridyl-substituted benzyloxybenzaldehydes by suzuki-miyaura coupling reactions

Hedvig Bölcskei, Andrea Német-Hanzelik, Zsófia Dubrovay, Viktor Háda, György Keglevich

Research output: Contribution to journalArticle

Abstract

Background: Aryl-methoxybenzaldehydes substituted in various positions may serve as valuable starting materials for the synthesis of biologically active compounds. Methods: Biaryl-methoxybenzaldehydes and pyridyl-aryl-methoxybenzaldehydes were synthesized by the Suzuki-Miyaura cross-coupling reactions as intermediates of potential drug substances. Three different catalytic approaches were compared. The classical Suzuki method utilising tetrakis(triphenylphosphine)palladium and sodium ethoxide, the protocol applying palladium acetate and tri(o-tolyl)phosphine, and the method using tetrakis(triphenylphosphine)palladium and cesium carbonate, were studied. Results: The selected boronic acids were the classical phenylboronic acid, as well as 4-pyridineand 3-pyridineboronic acids. 26 New biaryl-methoxybenzaldehydes or pyridyl-phenylmethoxybenzaldehydes have been synthesized, which may be intermediates for pharmaceutically active compounds. Conclusion: The method of Anderson et al. was preferred, because it provides satisfactory results in all cases.

Original languageEnglish
Pages (from-to)1248-1257
Number of pages10
JournalLetters in Drug Design and Discovery
Volume16
Issue number11
DOIs
Publication statusPublished - Jan 1 2019

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Palladium
phosphine
Boronic Acids
Cross Reactions
Acetates
Pharmaceutical Preparations
triphenylphosphine

Keywords

  • Biaryl-oxyaryl-aldehyde
  • Palladium acetate
  • Phenylboronic acid
  • Pyridineboronic acids
  • Suzuki-miyaura cross-coupling reaction
  • Tetrakis(triphenylphosphine)palladium

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery

Cite this

Synthesis of phenyl- and pyridyl-substituted benzyloxybenzaldehydes by suzuki-miyaura coupling reactions. / Bölcskei, Hedvig; Német-Hanzelik, Andrea; Dubrovay, Zsófia; Háda, Viktor; Keglevich, György.

In: Letters in Drug Design and Discovery, Vol. 16, No. 11, 01.01.2019, p. 1248-1257.

Research output: Contribution to journalArticle

Bölcskei, Hedvig ; Német-Hanzelik, Andrea ; Dubrovay, Zsófia ; Háda, Viktor ; Keglevich, György. / Synthesis of phenyl- and pyridyl-substituted benzyloxybenzaldehydes by suzuki-miyaura coupling reactions. In: Letters in Drug Design and Discovery. 2019 ; Vol. 16, No. 11. pp. 1248-1257.
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