Nucleophilic Reactivity of a Novel 3-Chloro-3-(4,9-dimethoxy5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal

Abstract

A novel 3-chloro-3-(4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal was synthesized from 6-acetyl-4,9-dimethoxy-5H-furo[3,2-g]chromen-5-one by the Vilsmeier–Haack reaction, and its chemical reactivity toward some mono- and di-nitrogen nucleophiles was investigated. The reactions of the synthesized enal with primary amines, specifically benzylamine and p-toluidine, gave novel enamines or enaminones, depending on the molar ratio of the reagents, and its reactions with 1,2- and 1,3-dinucleophiles produced some novel benzofuran derivatives bearing bipyrazole, pyrazolylisoxazole, and bipyrimidine substituents in the C6 position. The structures of the newly synthesized compounds waere elucidated on the basis of their analytical and spectral data.

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Funding

The authors extend their appreciation to the Deanship of Scientific Research, King Khalid University, for funding this work through the General Research Project (no. R.G.P1./22/40).

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Correspondence to T. E. Ali.

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Ali, T.E., Assiri, M.A., Ibrahim, M.A. et al. Nucleophilic Reactivity of a Novel 3-Chloro-3-(4,9-dimethoxy5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal. Russ J Org Chem 56, 845–855 (2020). https://doi.org/10.1134/S1070428020050188

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Keywords:

  • 6-acetylkhellin
  • Vilsmeier–Haack
  • β-chloroenaldehyde
  • nucleophilic reactions
  • benzofuran
  • pyrazole
  • isoxazole
  • pyrimidine