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Synthesis of 5,7-dihydroxy-4,8-dimethylchromen-2-one and its azo derivatives

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Abstract

5,7-Dihydroxy-4,8-dimethylchromen-2-one was synthesized based on methyl phloroglucinol and its spectral and physicochemical characteristics were obtained. Reactions of the newly synthesized coumarin with different diazonium salts were studied, conditions allowing selective obtaining the corresponding monoor bisazo compounds were found. The synthesized azo compounds dye nylon in the yellow-brown colors under standard coloration conditions, providing high stability of obtained colors upon exposure to physicochemical conditions.

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References

  1. T. P. Antsupova, Butlerovskie Soobshcheniya [Butlerov Communications], 2011, 27, No. 13, 63 (in Russian).

    Google Scholar 

  2. M. A. Al-Haiza, M. S. Mostafa, M. Y. El-Kady, Molecules, 2003, 8, 275.

    Article  CAS  Google Scholar 

  3. F. H. Dexeus, C. J. Logothetis, A. Sella, K. Fitz, R. Amato, J. M. Reuben, N. J. Dozier, J. Clin. Oncol., 1990, 8, 325.

    CAS  Google Scholar 

  4. H. Madari, D. Panda, L. Wilson, R. Jacobs, Cancer Res., 2003, 63, 1214.

    CAS  Google Scholar 

  5. D. Conley, E. M. Marshall, Proc. Am. Assoc. Canc. Res., 1987, 28, 63.

    Google Scholar 

  6. A. Z. Abyshev, R. A. Abyshev, S. V. Gadzikovskii, V. Kh. Nguen, V. A. Morozova, Butlerovskie Soobshcheniya [Butlerov Communications], 2013, 33, No. 1, 1 (in Russian).

    Google Scholar 

  7. I. Manolov, N. D. Danchev, Eur. J. Med. Chem. Chim. Ther., 1995, 30, 531.

    Article  CAS  Google Scholar 

  8. A. A. Emmanuel-Giota, K. C. Fylaktakidou, D. J. Hadjipavlou-Litina, K. E. Litinas, D. N. Nicolaides, J. Heterocycl. Chem., 2001, 38, 717.

    Article  CAS  Google Scholar 

  9. A. M. El-Agrody, M. S. Abd El-Latif, N. A. El-Hady, A. H. Fakery, A. H. Bedair, Molecules, 2001, 6, 519.

    Article  CAS  Google Scholar 

  10. G. Li, D. Wang, M. Sun, G. Li, J. Hu, Y. Zhang, Y. Yuan, H. Ji, N. Chen, G. Liu, J. Med. Chem., 2010, 53, 1741.

    Article  CAS  Google Scholar 

  11. N. R. Ayyangar, K. V. Srinivasan, T. Daniel, Dyes Pigments, 1991, 16, 197.

    Article  CAS  Google Scholar 

  12. N. R. Ayyangar, K. V. Srinivasan, T. Daniel, Dyes Pigments, 1990, 13, 301.

    Article  CAS  Google Scholar 

  13. Pat. RF 2292329; Byull. Isobret. [Invention Bull.], 2007, 3.

  14. F. M. Dean, E. Evans, A. Robertson, J. Chem. Soc., 1954, 4565.

    Google Scholar 

  15. J. A. Joule, K. Mills, Heterocyclic Chemistry, Blackwell Science, Oxford, 2000, 589 pp.

    Google Scholar 

  16. V. I. Ushkarov, K. I. Kobrakov, A. I. Alafinov, A. Kh. Shakhnes, S. A. Shevelev, Khim. Tekhnol. [Chem. Technol.], 2006, 7, No. 8, 5 (in Russian).

    Google Scholar 

  17. N. E. Bulusheva, Bazovyi laboratornyi praktikum po khimicheskoi tekhnologii voloknistykh materialov [Basic Laboratory Manual in Chemical Technology of Fibrous Materials], RIO MGTU, Moscow, 2000, 330 pp. (in Russian).

    Google Scholar 

  18. GOST 9733.4-83 Materialy tekstil’nye. Metod ispytaniya ustoichivosti okraski k stirkam [Textile Materials. Method for Testing of Color Stability to Washing], Izd-vo standardov, Moscow, 1985 (in Russian).

  19. GOST 9733.27-83 Materialy tekstil’nye. Metod ispytaniya ustoichivosti okraski k treniyu [Textile Materials. Method for Testing of Color Stability to Friction], Izd-vo standardov, Moscow, 1985 (in Russian).

  20. GOST 9733.6-83 Materialy tekstil’nye. Metod ispytaniya ustoichivosti okraski k potu [Textile Materials. Method for Testing of Color Stability to Sweat], Izd-vo standardov, Moscow, 1985 (in Russian).

  21. PASSOnline; http://www.pharmaexpert.ru/PASSOnline/ (last checked: 10.05.2013).

  22. G. S. Stankevich, T. I. Yakovenko, Laboratornyi praktikum po kursu "Khimiya krasitelei i tekstil’no-vspomogatel’nykh veshchestv" [Laboratory Manual on the Course "Chemical Dyes and Textile Auxiliaries"], RIO MGTU, Moscow, 2001, 60 pp. (in Russian).

    Google Scholar 

  23. A. V. El’tsov, Laboratornyi praktikum po sintezu promezhutochnykh produktov i krasitelei. Uchebnoe posobie dlya vuzov [Laboratory Manual on Synthesis of Intermediate Products and Dyes. Textbook for Higher Educational Institutions], Khimiya, Leningrad, 1985, 352 pp. (in Russian).

    Google Scholar 

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Authors and Affiliations

  1. Moscow State University of Design and Technology, 1 ul. Malaya Kaluzhskaya, 119991, Moscow, Russian Federation

    S. S. Bobylev, K. I. Kobrakov, D. N. Kuznetsov, A. G. Ruchkina & S. A. Shevelev

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. Kh. Shakhnes & A. N. Fakhrutdinov

Authors
  1. S. S. Bobylev
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  2. K. I. Kobrakov
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  3. D. N. Kuznetsov
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  4. A. G. Ruchkina
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  5. S. A. Shevelev
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  6. A. Kh. Shakhnes
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  7. A. N. Fakhrutdinov
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Corresponding author

Correspondence to D. N. Kuznetsov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0154–0160, January, 2015.

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Bobylev, S.S., Kobrakov, K.I., Kuznetsov, D.N. et al. Synthesis of 5,7-dihydroxy-4,8-dimethylchromen-2-one and its azo derivatives. Russ Chem Bull 64, 154–160 (2015). https://doi.org/10.1007/s11172-015-0836-3

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  • DOI: https://doi.org/10.1007/s11172-015-0836-3

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