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

Russian Journal of Organic Chemistry volume 56, pages2074–2078(2020)Cite this article

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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Fig. 1.

REFERENCES

  1. 1

    Kirillov, N.F. and Gavrilov, A.G., Russ. J. Gen. Chem., 2008, vol. 78, p. 1422. https://doi.org/10.1134/S1070363208070244

    CAS  Article  Google Scholar 

  2. 2

    Kirillov, N.F. and Gavrilov, A.G., Russ. J. Org. Chem., 2008, vol. 44, p. 963. https://doi.org/10.1134/S1070428008070051

    CAS  Article  Google Scholar 

  3. 3

    Kirillov, N.F., Makhmudov, R.R., Gavrilov, A.G., Mardanova, L.G., and Vakhrin, M.I., Pharm. Chem. J., 2013, vol. 47, p. 40. https://doi.org/10.1007/s11094-013-0892-7

    CAS  Article  Google Scholar 

  4. 4

    Nikiforova, E.A., Baibarodskikh, D.V., Kirillov, N.F., Dmitriev, M.V., and Shurov, S.N., Russ. J. Org. Chem., 2019, vol. 55, p. 339. https://doi.org/10.1134/S1070428019030114

    CAS  Article  Google Scholar 

  5. 5

    CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171.NET).

  6. 6

    Palatinus, L. and Chapuis, G., J. Appl. Crystallogr., 2007, vol. 40, p. 786. https://doi.org/10.1107/S0021889807029238

    CAS  Article  Google Scholar 

  7. 7

    Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    CAS  Article  Google Scholar 

  8. 8

    Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    CAS  Article  Google Scholar 

  9. 9

    Beilsteins Handbuch der organischen Chemie, EII, vol. 9, p. 9.

  10. 10

    Xiong, G., Liao, Y., Liu, X.-H., Tang, X., and Gong, Y., Tetrahedron, 2018, vol. 74, p. 1486. https://doi.org/10.1016/j.tet.2018.02.010

    CAS  Article  Google Scholar 

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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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  1. Perm State National Research University, 614990, Perm, Russia

    E. A. Nikiforova, D. V. Baibarodskikh, N. F. Kirillov, M. V. Dmitriev & D. P. Zverev

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  1. E. A. Nikiforova
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  2. D. V. Baibarodskikh
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  3. N. F. Kirillov
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  4. M. V. Dmitriev
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  5. D. P. Zverev
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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