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Conversion of Coumarins Accompanied by Opening and Recyclization of the Lactone Ring. 1. Study of the Reaction of 3-Ethoxycarbonyl(3-acyl)coumarins with Cyanoacetylhydrazine and Its Derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A stepwise sequence for the interaction of 3-ethoxycarbonyl(acyl)coumarins with cyanoacetylhydrazine, its N-acetyl and N-isopropylidene derivatives, leading to the formation of 3-cyanocoumarins, is proposed and demonstrated. It was established that the 3-cyanocoumarins formed are also able to participate in further conversions by a type of Michael reaction.

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REFERENCES

  1. V. D. Nageswara Sastry andT. R. Seshadri, Proc. Indian Acad. Sci., 16A, 29 (1942); Chem. Abstr., 37, 880 (1943).

    Google Scholar 

  2. A. Sammour,M. Abdalla, andM. Elkady, Acta Chim. Hung., 82, 369 (1974).

    Google Scholar 

  3. M. P. Nemeryuk,V. D. Dimitrova,A. L. Sedov, andV. F. Traven, Khim. Geterotsikl. Soedin., 1417 (1997).

  4. V. F. Traven,V. D. Dimitrova,A. L. Sedov,R. V. Rozhkov,M. P. Nemeryuk,M. R. Salem, andE. A. Carberry, Heterocycl. Commun., 4, 33 (1998).

    Google Scholar 

  5. P. B. Terentiev andA. P. Stankyavichus, Mass Spectrometric Analysis of Biologically Active Nitrogen Bases [in Russian], Mokslas, Vilnius (1987), p. 149.

    Google Scholar 

  6. C. N. O'Callaghan, J. Chem. Soc., C, 207 (1971).

  7. P. Czerney andH. Hartmann, J. Prakt. Chem., 323, 691 (1981).

    Google Scholar 

  8. Abdel-Kerim M. N. Gohar,F. F. Abdel-Latif, andM. S. El-Ktatny, Indian J. Chem., 25B, 404 (1986).

    Google Scholar 

  9. H. Junek andF. Frosch, Z. Naturforsch., 26B, 1124 (1971).

    Google Scholar 

  10. N. A. Ismail,F. A. Khalifa, andA. A. Magd El Din, Heterocycles, 32, 1101 (1991).

    Google Scholar 

  11. R. Clinging,F. M. Dean, andL. E. Houghten, J. Chem. Soc., C, 897 (1970).

  12. E. C. Horning andM. G. Horning, J. Am. Chem. Soc., 69, 968 (1947).

    Google Scholar 

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Authors and Affiliations

  1. D. I. Mendeleev Russian Chemical Engineering University, Moscow, 125047

    M. P. Nemeryuk, V. D. Dimitrova & V. F. Traven

  2. Center for Drug Chemistry - All Russian Chemical and Pharmaceutical Research Institute, Moscow, 119815, Russia

    O. S. Anisimova & N. P. Solov'eva

Authors
  1. M. P. Nemeryuk
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  2. V. D. Dimitrova
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  3. O. S. Anisimova
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  4. A. L. Sedov2
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  5. N. P. Solov'eva
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  6. V. F. Traven
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Nemeryuk, M.P., Dimitrova, V.D., Anisimova, O.S. et al. Conversion of Coumarins Accompanied by Opening and Recyclization of the Lactone Ring. 1. Study of the Reaction of 3-Ethoxycarbonyl(3-acyl)coumarins with Cyanoacetylhydrazine and Its Derivatives. Chemistry of Heterocyclic Compounds 39, 1454–1465 (2003). https://doi.org/10.1023/B:COHC.0000014410.73636.dd

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  • DOI: https://doi.org/10.1023/B:COHC.0000014410.73636.dd

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