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Reactions of zinc enolates derived from 1-aryl-2-bromo-alkanones and 1-aryl-2-bromo-2-phenylethanone with 3-aroyl-6-bromochromen-2-ones and 2-benzoylbenzo[f]chromen-3-one

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Abstract

3-Aroyl-6-bromochromen-2-ones and 2-benzoylbenzo[f]chromen-3-one reacted with zinc enolates derived from 1-aryl-2-bromoalkanones and 1-aryl-2-bromo-2-phenylethanone to give, respectively, 4-(1-alkyl-2-aryl-2-oxoethyl)-3-aroyl-6-bromochroman-2-ones and 1-(2-aroyl-1-methyl-2-oxoethyl)-2-benzoyl-1,2-dihydrobenzo[f]chromen-3-ones as a single stereoisomer. Treatment with acetic anhydride of the intermediate product obtained from 3-benzoyl-6-bromochromen-2-one and [1-(4-chlorophenyl)-2-phenylethen-1-yloxy]-zinc(II) bromide resulted in the formation of 3-(1-acetoxy-1-phenylmethylidene)-6-bromo-4-[2-(4-chlorophenyl)-2-oxo-1-phenylethyl]chroman-2-one.

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References

  1. Shchepin, V.V., Korzun, A.E., Shurov, S.N., Vakhrin, M.I., and Russkhikh, N.Yu., Russ. J. Gen. Chem., 2004, vol. 74, p. 1410.

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Authors and Affiliations

  1. Perm State University, ul. Bukireva 15, Perm, 614990, Russia

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

  2. Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, ul. S. Kovalevskoi 20, Yekaterinburg, 620219, 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. P. S. Silaichev
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  5. M. A. Ezhikova
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  6. M. I. Kodess
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Additional information

Original Russian Text © V.V. Shchepin, A.E. Korzun, M.I. Vakhrin, P.S. Silaichev, M.A. Ezhikova, M.I. Kodess, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 9, pp. 1362–1365.

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Shchepin, V.V., Korzun, A.E., Vakhrin, M.I. et al. Reactions of zinc enolates derived from 1-aryl-2-bromo-alkanones and 1-aryl-2-bromo-2-phenylethanone with 3-aroyl-6-bromochromen-2-ones and 2-benzoylbenzo[f]chromen-3-one. Russ J Org Chem 42, 1344–1347 (2006). https://doi.org/10.1134/S1070428006090156

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  • DOI: https://doi.org/10.1134/S1070428006090156

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