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The reaction of the disodium derivative of benzophenone with 2-bromopyridine

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of the disodium derivative of benzophenone with 2-bromopyridine in liquid ammonia results in the introduction of a diphenylhydroxymethyl group in the γ-position of the heterocyclic ring, followed by ammonolysis of the bromine in the resulting 2-bromodihydropyridine. The anomalous nature of this reaction results from the nature of the organometallic compound.

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References

  1. D. V. Ioffe, USSR patent no. 166927; Byull. izobr., no. 24, 1964.

  2. S. G. Kuznetsov and S. N. Golikov, Synthetic Atropine-like Substances [in Russian], Medgiz, 114, 1962.

  3. E. Sury and K. Hoffman, Helv. Chim., Acta, 37, 2133, 1954.

    Google Scholar 

  4. R. Lukes and I. Kuthan, Coll., 26, 1423, 1961.

    Google Scholar 

  5. R. Weiss and J. Ebert, Mon., 65, 399, 1935.

    Google Scholar 

  6. T. Grove, J. Am. Chem. Soc., 46, 1461, 1924.

    Google Scholar 

  7. M. Piantanida, J. pr. Chem., 153, 257, 1939.

    Google Scholar 

  8. H. Bohme and F. Soldan, Ber., 94, 3109, 1961.

    Google Scholar 

  9. A. Katritzky and D. Lagovskaya, The Chemistry of Heterocyclic Compounds [Russian translation], IL, Moscow, 109, 1963.

    Google Scholar 

  10. C. Wooster, J. Am. Chem. Soc., 50, 1388, 1928.

    Google Scholar 

  11. Organic Reactions [in Russian], 9, 7, 1959.

  12. D. V. Ioffe, collection ZhOKh: Biologically Active Compounds [in Russian], 147, 1965.

  13. D. V. Ioffe, ZhOKh, 35, 1851, 1965.

    Google Scholar 

  14. H. Hertog, H. Plas, M. Pieterse, and J. Streft, Rec. tray. chim., 84, 1569, 1965.

    Google Scholar 

  15. H. Hertog and H. Plas, Adv. Heterocycl. Chem., 4, 121, 1965.

    Google Scholar 

  16. US Patent no. 2804422; C. A., 52, 1558, 1958.

    Google Scholar 

  17. S. McElvain and K. Rorig, J. Am. Chem. Soc., 70, 1826, 1948.

    Google Scholar 

  18. N. Sperber, F. Villani, M. Sherlock, and D. Papa, J. Am. Chem. Soc., 73, 5010, 1951.

    Google Scholar 

  19. L. Anderson and N. Seeger, J. Am. Chem. Soc., 71, 345, 1949.

    Google Scholar 

  20. B. Z. Askinazi, D. V. Ioffe, and S. G. Kuznetsov, ZhOrKh, 4, 2003, 1968.

    Google Scholar 

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Authors
  1. D. V. Ioffe
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Additional information

Part X in the series “Reductive Metallation of Carbonyl Compounds”. For part IX, see [20].

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Ioffe, D.V. The reaction of the disodium derivative of benzophenone with 2-bromopyridine. Chem Heterocycl Compd 6, 46–50 (1970). https://doi.org/10.1007/BF00475422

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