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Reactions of Zinc Enolates Formed from 1-Aryl-2-bromo-2-phenylethanone or 2-Bromoindanone and Zinc, with Dimethyl 2-(1-Arylmethylene)malonates

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Abstract

Zinc enolates formed from 1-aryl-2-bromo-2-phenylethanones and zinc react with dimethyl 2-(1-arylmethylene)malonates to afford dimethyl 2-(1,3-diaryl-3-oxo-2-phenylpropyl)malonates. The latter react with cyclohexylamine, piperidine, or morpholine to give the corresponding monosubstituted amides. The zinc enolate derived from 2-bromoindanone and zinc reacts with dimethyl 2-(4-bromobenzylidene)malonate, yielding dimethyl 2-[(4-bromophenyl)(1-oxoindan-2-yl)methyl]malonate. The final products largely form as a single diastereomer.

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REFERENCES

  1. Fahmy, A.F., Mohamed, M.M., Arify, A.A., El Kady, M.Y., and El Hashash, M.A., Rev. Roum. Chim., 1980, vol. 25, no.1, p. 125.

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Authors and Affiliations

  1. Perm State University, Perm, Russia

    V. V. Shchepin, A. E. Korzun, M. I. Vakhrin, S. N. Shurov & P. S. Silaichev

  2. Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, Yekaterinburg, Russia

    M. A. Ezhikova & M. I. Kodess

Authors
  1. V. V. Shchepin
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  2. A. E. Korzun
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  3. M. I. Vakhrin
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  4. S. N. Shurov
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  5. P. S. Silaichev
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  6. M. A. Ezhikova
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  7. M. I. Kodess
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Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 12, 2005, pp. 2026–2029.

Original Russian Text Copyright © 2005 by Shchepin, Korzun, Vakhrin, Shurov, Silaichev, Ezhikova, Kodess.

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Shchepin, V.V., Korzun, A.E., Vakhrin, M.I. et al. Reactions of Zinc Enolates Formed from 1-Aryl-2-bromo-2-phenylethanone or 2-Bromoindanone and Zinc, with Dimethyl 2-(1-Arylmethylene)malonates. Russ J Gen Chem 75, 1935–1938 (2005). https://doi.org/10.1007/s11176-006-0017-z

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  • DOI: https://doi.org/10.1007/s11176-006-0017-z

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