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Structure and condensation reactions of 2,3-dihydrofuro[3,2-c]coumarin-3-one

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Abstract

2,3-Dihydrofuro[3,2-c]coumarin-3-one was synthesized in quantitative yield from 3-(ω-bromoacetyl)-4-hydroxycoumarin in the presence of nucleophiles (including solvents). This compound undergoes keto-enol tautomerization and easily reacts with aromatic and heteroaromatic aldehydes to form crotonization products having a Z configuration and exhibiting strong fluorescence.

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References

  1. U. Brackman, Laser Dyes, Lamdachrome, Data Sheets, 2nd ed., Göttingen, Germany, 1997, p. 268.

  2. R. P. Haugland, Handbook of Fluorescent Probes and Research Chemical, Ed. M. T. Z. Spence, Molecular Probes, Inc., Eugene, USA, 1996.

    Google Scholar 

  3. A. Guiotto, P. Rodighiero, P. Manzini, G. Pastorini, F. Bordin, F. Baccichetti, F. Carlassare, D. Vedaldi, F. Dall’Acqua, M. Tamaro, G. Recchia, M. Cristofolini, J. Med. Chem., 1984, 27, 959.

    Article  CAS  Google Scholar 

  4. D. Vedaldi, F. Dall’Acqua, F. Baccichetti, F. Carlassare, F. Bordin, P. Rodighiero, P. Manzini, A. Guiotto, Farmaco, 1991, 46, 1381.

    CAS  Google Scholar 

  5. V. F. Traven, D. V. Kravtchenko, T. A. Chibisova, S. V. Shorshnev, Heterocycl. Commun., 1996, 2, 345.

    Article  CAS  Google Scholar 

  6. V. F. Traven, R. V. Rozhkov, A. Yu. Tolmachev, N. A. Kuznezova, N. Ya. Podhaluzina, E. A. Carberry, Heterocycl. Commun., 1997, 3, 339.

    Article  CAS  Google Scholar 

  7. O. B. Safronova, D. V. Kravchenko, I. N. Senchenya, V. F. Traven, Zh. Obshch. Khim., 2001, 71, 588 [Russ. J. Gen. Chem. (Engl. Transl.), 2001, 71].

    Google Scholar 

  8. D. V. Kravtchenko, T. A. Chibisova, V. F. Traven, Heterocycl. Commun., 1997, 3, 331.

    CAS  Google Scholar 

  9. V. F. Traven, I. I. Sakharuk, D. V. Kravchenko, A. V. Ivashchenko, Khim. Geterotsikl. Soedin., 2001, 312 [Chem. Hetherocycl. Compd. (Engl. Transl.), 2001].

  10. A. V. Manaev, T. A. Chibisova, K. A. Lyssenko, M. Yu. Antipin, V. F. Traven, Izv. Akad. Nauk, Ser. Khim., 2006, 2012 [Russ. Chem. Bull., Int. Ed., 2006, 55, 2091].

  11. A. V. Manaev, T. A. Chibisova, V. F. Traven, Izv. Akad. Nauk, Ser. Khim., 2006, 2144 [Russ. Chem. Bull., Int. Ed., 2006, 55, 2226].

    Google Scholar 

  12. M. Trkovnik, N. Zivkovic, M. Kules, R. Djudjic, Org. Prep. Proced. Int., 1978, 10, 215.

    Article  CAS  Google Scholar 

  13. V. F. Traven, D. V. Kravtchenko, T. A. Chibisova, S. V. Shorshnev, Mendeleev Commun., 1997, 249.

  14. O. Y. Borbulevych, R. D. Clarc, A. Romero, L. Tan, M. Y. Antipin, V. N. Nesterov, B. H. Cardelino, C. E. Moore, M. Sanghadasa, T. V. Timofeeva, J. Mol. Struct., 2002, 604, 73.

    Article  CAS  Google Scholar 

  15. A. S. Batsanov, J. C. Collings, R. M. Ward, A. E. Goeta, L. Porrés, A. Beeby, J. A. K. Howard, J. W. Steed, T. B. Marder, Cryst. Eng. Commun., 2006, 8, 622.

    CAS  Google Scholar 

  16. G. M. Sheldrick, SHELXS 97, SHELXL 97, University of Göttingen, Göttingen, Germany, 1997.

  17. E. R. Eisenhauer, K. P. Link, J. Am. Chem. Soc., 1953, 75, 2044.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. D. I. Mendeleev University of Chemical Technology of Russia, 9 pl. Miusskaya, 125047, Moscow, Russian Federation

    N. A. Kondratova & V. F. Traven

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    O. N. Kazheva, A. N. Chekhlov & O. A. D’yachenko

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    G. G. Aleksandrov

Authors
  1. N. A. Kondratova
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  2. O. N. Kazheva
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  3. G. G. Aleksandrov
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  4. A. N. Chekhlov
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  5. O. A. D’yachenko
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  6. V. F. Traven
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Corresponding author

Correspondence to V. F. Traven.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1873–1883, September, 2011.

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Kondratova, N.A., Kazheva, O.N., Aleksandrov, G.G. et al. Structure and condensation reactions of 2,3-dihydrofuro[3,2-c]coumarin-3-one. Russ Chem Bull 60, 1906–1916 (2011). https://doi.org/10.1007/s11172-011-0287-4

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  • DOI: https://doi.org/10.1007/s11172-011-0287-4

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