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Efficient synthetic approach to 1-aza- and 1,2,4-triazatriptycenes

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Convenient methods for the preparation of (het)aryl-substituted derivatives of 1-azatriptycene, including the cyclopentene-condensed analog, were proposed using the “1,2,4-triazine” methodology. The 1,2,4-triazatriptycene derivatives were synthesized for the first time. New original ligands of the 2,2′-bipyridine series are among the synthesized compounds.

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  1. C.-F. Chen, Y.-X. Ma, Iptycenes Chemistry: From Synthesis to Applications, Springer-Verlag, Berlin—Heidelberg, 2013; DOI:

    Book  Google Scholar 

  2. A. L. Schleper, C.-C. A. Voll, J. U. Engelhart, T. M. Swager, Synlett, 2017, 28, 2783; DOI:

    Article  CAS  Google Scholar 

  3. K. Kawasumi, T. Wu, T. Zhu, H. S. Chae, T. V. Voorhis, M. A. Baldo, T. M. Swager, J. Am. Chem. Soc., 2015, 137, 11908; DOI:

    Article  CAS  PubMed  Google Scholar 

  4. Q. Mei, L. Liu, J. Yang, X. Jiang, S. Ye, L. Zhang, B. Tong, Dyes and Pigments, 2022, 199, 110075; DOI:

    Article  CAS  Google Scholar 

  5. F. S. Benneckendorf, V. Rohnacher, E. Sauter, S. Hillebrandt, M. Münch, C. Wang, S. Casalini, K. Ihrig, S. Beck, D. Jänsch, J. Freudenberg, W. Jaegermann, P. Samorì, A. Pucci, U. H. F. Bunz, M. Zharnikov, K. Müllen, ACS Appl. Mater. Interfaces, 2020, 12, 6565; DOI:

    Article  CAS  PubMed  Google Scholar 

  6. E. M. Veen, P. M. Postma, H. T. Jonkman, A. L. Spek, B. L. Feringa, Chem. Commun., 1999, 1709; DOI:

  7. G. Kempter, D. Heilmann, M. Mühlstädt, J. Prakt. Chem., 1972, 314, 543; DOI:

    Article  CAS  Google Scholar 

  8. H. Quast, N. Schon, Liebigs Ann. Chem., 1984, 2, 381.

    Article  Google Scholar 

  9. J. H. Markgraf, I. J. Leonard, M. E. Morrison, C. R. Rilyers, Heterocycles, 1989, 29, 649; DOI:

    Article  CAS  Google Scholar 

  10. J. H. Markgraf, H. A. Davis, P. S. Ernst, K. S. Hirsch, K. J. Leonard, M. E. Morrison, C. R. Myers, Tetrahedron, 1991, 47, 183; DOI:

    Article  CAS  Google Scholar 

  11. J. H. Markgraf, P. K. Sangani, R. J. Manalansan, S. A. Snyder, R. P. Thummel, J. Chem. Res., Synopses, 2000, 12, 561.

    Article  Google Scholar 

  12. A. M. Prokhorov, D. N. Kozhevnikov, Chem. Heterocycl. Compd., 2012, 48, 1153; DOI:

    Article  CAS  Google Scholar 

  13. G. R. Pabst, O. C. Pfüller, J. Sauer, Tetrahedron, 1999, 55, 8045; DOI:

    Article  CAS  Google Scholar 

  14. A. Rykowski, D. Branowska, J. Kielak, Tetrahedron Lett., 2000, 41, 3657; DOI:

    Article  CAS  Google Scholar 

  15. A. F. Khasanov, D. S. Kopchuk, I. L. Nikonov, O. S. Taniya, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, Russ. Chem. Bull., 2021, 70, 999; DOI:

    Article  CAS  Google Scholar 

  16. F. H. Case, J. Org. Chem., 1965, 30, 931; DOI:

    Article  CAS  Google Scholar 

  17. M. O’Rourke, S. A. Lang, Jr., E. Cohen, J Med. Chem., 1977, 20, 723; DOI:

    Article  PubMed  Google Scholar 

  18. I. Pyka, J. Nikl, D. Schollmeyer, S. R. Waldvogel, Eur. J. Org. Chem., 2017, 24, 3501; DOI:

    Article  Google Scholar 

  19. V. N. Kozhevnikov, M. M. Ustinova, P. A. Slepukhin, A. Santoro, D. W. Bruce, D. N. Kozhevnikov, Tetrahedron Lett., 2008, 49, 4096; DOI:

    Article  CAS  Google Scholar 

  20. G. V. Zyryanov, D. S. Kopchuk, I. S. Kovalev, E. V. Nosova, V. L. Rusinov, O. N. Chupakhin, Russ. Chem. Rev., 2014, 83, 783; DOI:

    Article  Google Scholar 

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This work was financially supported by the Russian Science Foundation (Project No. 21-13-00304) and Council on Grants at the President of the Russian Federation (Project No. NSh-1223.2022.1.3).

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Correspondence to D. S. Kopchuk.

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No human or animal subjects were used in this research.

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The authors declare no competing interests.

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Based on the materials of the VII International Conference “Modern Synthetic Methodologies for Creating Drugs and Functional Materials” (MOSM 2023) dedicated to the 125th birth anniversary of Academician I. Ya. Postovsky (September 10–16, 2023, Yekaterinburg—Perm, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 12, pp. 3032–3036, December, 2023

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Rybakova, S.S., Valieva, M.I., Kudryashova, E.A. et al. Efficient synthetic approach to 1-aza- and 1,2,4-triazatriptycenes. Russ Chem Bull 72, 3032–3036 (2023).

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