Reformatsky Reaction of 1-Aryl-3-(2-hydroxyphenyl)prop-2-en-1-ones with Methyl 1-Bromocyclohexanecarboxylate

Abstract

1-Aryl-3-(2-hydroxy-5-R-phenyl)prop-2-en-1-ones reacted with the Reformatsky reagent derived from methyl 1-bromocyclohexanecarboxylate to give 4-(2-aryl-2-oxoethyl)-6-R-2H,4H-spiro[[1]benzopyran-3,1′-cyclohexan]-2-ones. The products are formed as a result of intramolecular cyclization of the adduct of the organozinc reagent and substituted chalcone via nucleophilic attack of the phenoxide oxygen atom on the ester carbonyl carbon atom. No cyclization products resulting from attack of the enolate oxygen atom on the ester carbonyl carbon atom were detected.

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Scheme
Fig. 1.

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Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 18-33-00509) and by the Government of Perm Krai.

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Correspondence to E. A. Nikiforova.

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Nikiforova, E.A., Baibarodskikh, D.V., Kirillov, N.F. et al. Reformatsky Reaction of 1-Aryl-3-(2-hydroxyphenyl)prop-2-en-1-ones with Methyl 1-Bromocyclohexanecarboxylate. Russ J Org Chem 56, 2074–2078 (2020). https://doi.org/10.1134/S1070428020120040

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Keywords:

  • Reformatsky reaction
  • 1-bromocycloalkanecarboxylates
  • 1-bromocyclohexanecarboxylate
  • spiro heterocycles
  • chroman-2-ones
  • hydroxy chalcones
  • spiro chromanones