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A new reaction of the phenylhydrazones of 1,5-diketones. Synthesis of dihydropyran derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It was shown that the monophenylhydrazones of 1,5-diketones are converted by reduction with borohydride followed by treatment of the obtained hydrazino alcohols with acidic agents into derivatives of dihydropyran with the elimination of phenylhydrazine as the respective salt. γ,δ-Unsaturated ketones were isolated as side products of this reaction. The ways in which these compounds are formed are discussed.

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References

  1. T. V. Moskovkina and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 46 (1986).

  2. T. V. Moskovkina and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 822 (1983).

  3. T. V. Moskovkina and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 645 (1976).

  4. T. V. Moskovkina, Khim. Geterotsikl. Soedin., 1355 (2002).

  5. T. V. Moskovkina, T. V. Pyanzin, and V. V. Isakov, Khim. Geterotsikl. Soedin., 281 (2001).

  6. A. Sera, M. Ohara, H. Yamada, E. Egashira, N. Ueda, and J. Setsune, Bull. Chem. Soc. Jpn., 67, 1912 (1994).

    CAS  Google Scholar 

  7. W. G. Dauben and H. O. Krabbenhoft, J. Org. Chem., 42, 282 (1977).

    CAS  Google Scholar 

  8. R. I. Longley, Jr. and W. S. Emerson, J. Am. Chem. Soc., 72, 3079 (1950).

    Article  CAS  Google Scholar 

  9. G. Dujardin, M. Maudet, and E. Brown, Tetrahedron Lett., 35, 8619 (1994).

    Article  CAS  Google Scholar 

  10. M. Trolliet, R. Longegari, and J. Dreux, Bull. Soc. Chim. France, 1484 (1974).

  11. V. G. Kharchenko, N. V. Pchelintseva, L. I. Markova, and O. V. Fedotova, Khim. Geterotsikl. Soedin., 1155 (2000).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 26–31, January, 2006.

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Moskovkina, T.V. A new reaction of the phenylhydrazones of 1,5-diketones. Synthesis of dihydropyran derivatives. Chem Heterocycl Compd 42, 22–27 (2006). https://doi.org/10.1007/s10593-006-0041-2

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  • DOI: https://doi.org/10.1007/s10593-006-0041-2

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