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The Extension of Conjugated System in Pyridyl-Substituted Monoazatriphenylenes for the Tuning of Photophysical Properties

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Chemistry of Heterocyclic Compounds Aims and scope

We propose a method for the synthesis of diaryl-substituted pyridylmonoazatriphenylenes by the heterocyclization reaction of dihalosubstituted phenanthrenequinones with pyridine-2-carboxylic acid amidrazone, followed by aza-Diels–Alder reaction and Suzuki cross coupling. The obtained compounds showed more promising photophysical properties, compared to non-arylated analogs.

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References

  1. B. H. Bakker, M. Goes, N. Hoebe, H. J. van Ramesdonk, J. W. Verhoeven, M. H. V. Werts, and J. W. Hofstraat, Coord. Chem. Rev., 208, 3 (2000).

    Article  CAS  Google Scholar 

  2. T. R. Govindachari, N. Viswanathan, J. Radhakrishnan, R. Charubala, N. Nityanandra Rao, and B. R. Pai, Indian J. Chem., 11, 1215 (1973).

    CAS  Google Scholar 

  3. T. R. Govindachari, B. R. Pai, and K. Nagarajan, J. Chem. Soc., 2801 (1954).

  4. C. W. Lim, O. Tissot, A. Mattison, M. W. Hooper, J. M. Brown, A. R. Cowley, D. I. Hulmes, and A. J. Blacker, Org. Process Res. Dev., 7, 379 (2003).

    Article  CAS  Google Scholar 

  5. B. A. Sweetman, H. Muller-Bunz, and P. J. Guiry, Tetrahedron Lett., 46, 4643 (2005).

    Article  CAS  Google Scholar 

  6. D. S. Kopchuk, I. N. Egorov, T. A. Tseitler, A. F. Khasanov, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., 538 (2013). [Chem. Heterocycl. Compd., 49, 503 (2013).]

    Article  CAS  Google Scholar 

  7. V. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, M. M. Ustinova, B. Koenig, and D. N. Kozhevnikov, Tetrahedron, 64, 8963 (2008).

    Article  CAS  Google Scholar 

  8. A. H. Younes, L. Zhang, R. J. Clark, and L. Zhu, J. Org. Chem., 74, 8761 (2009).

    Article  CAS  Google Scholar 

  9. H. S. Joshi, R. Jamshidi, and Y. Tor, Angew. Chem., Int. Ed., 38, 2722 (1999).

    CAS  Google Scholar 

  10. J. C. Loren and J. S. Siegel, Angew. Chem., Int. Ed., 40, 754 (2001).

    Article  CAS  Google Scholar 

  11. G. Albano, V. Balzani, E. C. Constable, M. Maestri, and D. R. Smith, Inorg. Chim. Acta, 277, 225 (1998).

    Article  CAS  Google Scholar 

  12. W. Goodall and J. A. G. Williams, Chem. Commun., 2514 (2001).

  13. F. Hershnann, Ber. Dtsch. Chem. Ges., 41, 1998 (1908).

    Article  Google Scholar 

  14. M. Krueger and E. Mosettig, J. Org. Chem., 5, 313 (1940).

    Article  CAS  Google Scholar 

  15. N. P. Buu-Hoi, J. Org. Chem., 19, 721 (1954).

    Article  CAS  Google Scholar 

  16. W. Marckwald, Justus Liebigs Ann. Chem., 274, 331 (1893).

    Article  Google Scholar 

  17. P. J. Campos, E. Anon, M. C. Malo, and M. A. Rodriguez, Tetrahedron, 54, 14113 (1998).

    Article  CAS  Google Scholar 

  18. O. Bilgic and D. W. Young, J. Chem. Soc., Perkin Trans. 1, 1233 (1980).

  19. D. N. Nicolaides, K. E. Litinas, G. K. Papageorgiou, and J. Stephanidou-Stephanatou, J. Heterocycl. Chem., 28, 139 (1991).

    Article  CAS  Google Scholar 

  20. I. Nagao, M. Shimizu, and T. Hiyama, Angew. Chem., Int. Ed., 48, 7573 (2009).

    Article  CAS  Google Scholar 

  21. A. McIver, D. D. Young, and A. Deiters, Chem. Commun., 4750 (2008).

  22. G. R. Pabst, O. C. Pfüller, and J. Sauer, Tetrahedron, 55, 8045 (1999).

    Article  CAS  Google Scholar 

  23. A. Rykowski, D. Branowska, and J. Kielak, Tetrahedron Lett., 41, 3657 (2000).

    Article  CAS  Google Scholar 

  24. D. S. Kopchuk, A. F. Khasanov, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, and O. N. Chupakhin, Mendeleev Commun., 23, 209 (2013).

    Article  CAS  Google Scholar 

  25. E. C. Taylor, J. E. Macor, and J. L. Pont, Tetrahedron, 43, 5145 (1987).

    Article  CAS  Google Scholar 

  26. D. S. Kopchuk, G. V. Zyryanov, I. S. Kovalev, A. F. Khasanov, A. S. Medvedevskikh, V. L. Rusinov, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., 535 (2013). [Chem. Heterocycl. Compd., 49, 500 (2013).]

    Article  CAS  Google Scholar 

  27. E. K. Unver, S. Tarkuc, C. Tanyeli, L. Toppare, and Y. A. Udum, J. Polym. Sci., Part A: Polym. Chem., 48, 1714 (2010).

    Article  CAS  Google Scholar 

  28. F. Dewhurst and P. K. J. Shah, J. Chem. Soc. C, 1503 (1969).

  29. P. Luliński and L. Skulski, Bull. Chem. Soc. Jpn., 72, 115 (1999).

    Article  Google Scholar 

  30. D. Chaudhuri, K. J. van Schooten, S. Liu, J. M. Lupton, H. Wettach, E. Sigmund, and S. Höger, Angew. Chem., Int. Ed., 49, 7714 (2010).

    Article  CAS  Google Scholar 

  31. K. Brunner, A. van Dijken, H. Börner, J. J. A. M. Bastiaansen, N. M. M. Kiggen, and B. M. W. Langeveld, J. Am. Chem. Soc., 126, 6035 (2004).

    Article  CAS  Google Scholar 

  32. S. C. De, Q. J. Indian Chem. Soc., 4, 183 (1927).

    CAS  Google Scholar 

  33. J. Schmidt and H. Bürkert, Ber. Dtsch. Chem. Ges., 1356 (1927).

  34. S. C. De, J. Indian Chem. Soc., 7, 361 (1930).

    CAS  Google Scholar 

  35. F. H. Case, J. Org. Chem., 30, 931 (1965).

    Article  CAS  Google Scholar 

  36. V. N. Kozhevnikov, M. M. Ustinova, P. A. Slepukhin, A. Santoro, D. W. Bruce, and D. N. Kozhevnikov, Tetrahedron Lett., 49, 4096 (2008).

    Article  CAS  Google Scholar 

  37. D. S. Kopchuk, A. F. Khasanov, I. S. Kovalev, G. A. Kim, I. L. Nikonov, G. V. Zyryanov, V. L. Rusinov, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., 936 (2014). [Chem. Heterocycl. Compd., 50, 864 (2014).]

    Article  Google Scholar 

  38. S. Parker, Photoluminescence of Solutions [Russian translation], Mir, Moscow (1972), p. 251.

    Google Scholar 

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The work was performed with support from the Ministry of Education and Science of the Russian Federation (state contract 8430), Grants Council of the President of Russian Federation (grant MK 1511.2013.3), as well as the Program 211 of the Government of the Russian Federation (contract No. 02.А03.21.0006).

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Authors and Affiliations

  1. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg, 620002, Russia

    D. S. Kopchuk, A. F. Khasanov, I. S. Kovalev, G. V. Zyryanov, G. A. Kim, I. L. Nikonov, V. L. Rusinov & O. N. Chupakhin

  2. I. Ya. Postovskii Institute of Organic Synthesis, 22 S. Kovalevskoi St./20 Akademicheskaya St., Yekaterinburg, 620219, Russia

    D. S. Kopchuk, G. V. Zyryanov, G. A. Kim, V. L. Rusinov & O. N. Chupakhin

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  1. D. S. Kopchuk
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  2. A. F. Khasanov
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  3. I. S. Kovalev
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  4. G. V. Zyryanov
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  5. G. A. Kim
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  6. I. L. Nikonov
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  7. V. L. Rusinov
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  8. O. N. Chupakhin
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Corresponding author

Correspondence to G. V. Zyryanov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 943-952, June, 2014.

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Kopchuk, D.S., Khasanov, A.F., Kovalev, I.S. et al. The Extension of Conjugated System in Pyridyl-Substituted Monoazatriphenylenes for the Tuning of Photophysical Properties. Chem Heterocycl Comp 50, 871–879 (2014). https://doi.org/10.1007/s10593-014-1541-0

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  • DOI: https://doi.org/10.1007/s10593-014-1541-0

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