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One-step synthesis of 1,4-bis(het)arylisoquinolines by the reaction of 1,2,4-triazines with arynes

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 3,6-bis(het)aryl-1,2,4-triazines (hetaryl ≠ 2-pyridyl) with aryne intermediates generated in situ was studied. As a result, novel 1,4-bis(het)arylisoquinolines were synthesized with yields of up to 45%. The main rules of the reactions were studied, and the obtained experimental data were compared with those described in the literature.

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References

  1. (a) Heterocycles in Natural Product Synthesis; Majumdar, K. C.; Chattopadhyay, S. K., Eds.; Wiley-VCH: Weinheim, 2011. (b) The Chemistry of Heterocyclic Compounds; Coppola, G. M.; Schuster, H. F.; Wiley: New York, 1981, Vol. 38, Part 3, p. 552.

  2. Merck, G. Ann. Chem. Pharm. 1848, 66, 125.

    Article  Google Scholar 

  3. (a) Handley, D. A.; Van Valen, R. G.; Melden, M. K.; Houlihan, W. J.; Saunders, R. N. J. Pharmacol. Exp. Ther. 1988, 247, 617. (b) Houlihan, W. J.; Cheon, S. H.; Parrino, V. A.; Handley, D. A.; Larson, D. A. J. Med. Chem. 1993, 36, 3098. (c) Scholz, D.; Schmidt, H.; Prieschl, E. E.; Csonga, R.; Scheirer, W.; Weber, V.; Lembachner, A.; Seidl, G.; Werner, G.; Mayer, P.; Baumruker, T. J. Med. Chem. 1998, 41, 1050. (d) Griffin, R. J.; Fontana, G.; Golding, B. T.; Guiard, S.; Hardcastle, I. R.; Leahy, J. J. J.; Martin, N.; Richardson, C.; Rigoreau, L.; Stockley, M.; Smith, G. C. M. J. Med. Chem. 2005, 48, 569.

  4. (a) Iwasa, K.; Moriyasu, M.; Tachibana, Y.; Kim, H. S.; Wataya, Y.; Wiegrebe, W.; Bastow, K. F.; Cosentino, L. M.; Kozuka, M.; Lee, K. H. Bioorg. Med. Chem. 2001, 9, 2871. (b) Miller, J. F.; Gudmundsson, K. S.; D'Aurora Richardson, L.; Jenkinson, S.; Spaltenstein, A.; Thomson, M.; Wheelan, P. Bioorg. Med. Chem. Lett. 2010, 20, 3026. (c) Kashiwada, Y.; Aoshima, A.; Ikeshiro, Y.; Chen, Y.-P.; Furukawa, H.; Itoigawa, M.; Fujioka, T.; Mihashi, K.; Cosentino, L. M.; Morris-Natschke, S. L.; Lee, K. H. Bioorg. Med. Chem. 2005, 13, 443.

  5. (a) Mukherjee, A.; Dutta, S.; Sanyal, U. J. Cancer Res. Ther. 2013, 9, 442. (b) Fontana, A.; Cavaliere, P.; Wahidulla, S.; Naik, C. G.; Cimino, G. Tetrahedron2000, 56, 7305.

  6. (a) Jiang, Y.; Kong, W.; Shen, Y.; Wang, B. Tetrahedron2015, 71, 5584. (b) Kho, Y.-M.; Shin, E. J. Molecules2017, 22, 1569.

  7. (a) Halder, S.; Ghosh, P.; Hazra, A.; Banerjee, P.; Roy, P. New J. Chem. 2018, 42, 8408. (b) Ma, Y.; Hao, Li, H.; Peng, S.; Wang, L. Anal. Chem. 2012, 84, 8415. (с) Zyryanov, G. V.; Kopchuk, D. S.; Kovalev, I. S.; Nosova, E. V.; Rusinov, V. L.; Chupakhin, O. N. Russ. Chem. Rev. 2014, 83, 783. [Usp. Khim.2014, 83, 783.]

  8. (a) Kumar, N. S.; Rao, L. C.; Babu, N. J.; Meshram, H. M. RSC Adv. 2015, 5, 95539. (b) Roya, B.; Hazraab, P. J. Mol. Liq. 2018, 261, 520. (c) Zhao, Y.; Zhang, G.; Liu, Z.; Guo, C.; Peng, C.; Pei, M.; Li, P. J. Photochem. Photobiol., A2016, 314, 52. d Li, G.; Zhu, D.; Xue, L.; Jang, H. Org. Lett. 2013, 15, 5020.

  9. (a) Rotzoll, S.; Willy, B.; Schönhaber, J.; Rominger, F.; Müller, T. J. J. Eur. J. Org. Chem. 2010, 3516. (b) Woody, K. B.; Henry, E. M.; Jagtap, S.; Collard, D. M. Macromolecules2011, 44, 9118. (c) Schaffroth, M.; Lindner, B. D.; Vasilenko, V.; Rominger, F.; Bunz, U. H. F. J. Org. Chem. 2013, 78, 3142. (d) Kopchuk, D. S.; Khasanov, A. F.; Kim, G. A.; Nosova, E. V.; Zyryanov, G. V.; Kovalev, I. S.; Rusinov, V. L.; Chupakhin, O. N. Russ. Chem. Bull., Int. Ed. 2015, 64, 872. [Izv. Akad. Nauk, Ser. Khim.2015, 872.] (e) Moni, L.; Gers-Panther, C. F.; Anselmo, M.; Müller, T. J. J.; Riva, R. Chem.–Eur. J. 2016, 22, 2020.

  10. (a) Pomeranz, C. Monatsh. Chem. 1893, 14, 116. (b) Bischler, A.; Napieralski, B. Ber. Dtsch. Chem. Ges. 1893, 26, 190. (c) Comprehensive Organic Name Reactions and Reagents; Wang, Z., Ed.; Wiley-Interscience: New Jersey, 2010, p. 2206. c Doi, S.; Shirai, N.; Sato, Y. J. Chem. Soc., Perkin Trans. 1997, 1, 2217. (e) Comprehensive Organic Name Reactions and Reagents; Wang, Z., Ed.; Wiley-Interscience: New Jersey, 2010, p. 544. d Loones, K. T. J.; Maes, B. U. W.; Dommisse, R. A.; Lemiere, G. L. F. Chem. Commun. 2004, 2466. e Sharon, A.; Pratap, R.; Maulik, P. R.; Ram, V. J. Tetrahedron2005, 61, 3781.

  11. Kopchuk, D. S.; Kovalev, I. S.; Khasanov, A. F.; Zyryanov, G. V.; Slepukhin, P. A.; Rusinov, V. L.; Chupakhin, O. N. Mendeleev Commun. 2013, 23, 142.

    Article  CAS  Google Scholar 

  12. (a) Kopchuk, D. S.; Chepchugov, N. V.; Khasanov, A. F.; Kovalev, I. S.; Santra, S.; Nosova, E. V.; Zyryanov, G. V.; Majee, A.; Rusinov, V. L.; Chupakhin, O. N. Tetrahedron Lett. 2016, 57, 3862. (b) Kopchuk, D. S.; Nikonov, I. L.; Zyryanov, G. V.; Nosova, E. V.; Kovalev, I. S.; Slepukhin, P. A.; Rusinov, V. L.; Chupakhin, O. N. Mendeleev Commun. 2015, 25, 13. (c) Kopchuk, D. S.; Nikonov, I. L.; Zyryanov, G. V.; Kovalev, I. S.; Taniya, O. S.; Rusinov, V. L.; Chupakhin, O. N. Russ. J. Org. Chem. 2015, 51, 1170. [Zh. Org. Khim.2015, 51, 1189.] (d) Nikonov, I. L.; Kopchuk, D. S.; Kovalev, I. S.; Zyryanov, G. V.; Khasanov, A. F.; Slepukhin, P. A.; Rusinov, V. L.; Chupakhin, O. N. Tetrahedron Lett. 2013, 54, 6427.

  13. (a) Kopchuk, D. S.; Nikonov, I. L.; Zyryanov, G. V.; Kovalev, I. S.; Rusinov, V. L.; Chupakhin, O. N. Chem. Heterocycl. Compd. 2014, 50, 907. [Khim. Geterotsikl. Soedin.2014, 983.] (b) Kopchuk, D. S.; Krinochkin, A. P.; Khasanov, A. F.; Kovalev, I. S.; Slepukhin, P. A.; Starnovskaya, E. S.; Mukherjee, A.; Rahman, M.; Zyryanov, G. V.; Majee, A.; Rusinov, V. L.; Chupakhin, O. N.; Santra, S. Synlett2018, 483. (с) Kopchuk, D. S.; Nikonov, I. L.; Krinochkin, A. P.; Kovalev, I. S.; Zyryanov, G. V.; Rusinov, V. L.; Chupakhin, O. N. Russ. J. Org. Chem. 2017, 53, 959. [Zh. Org. Khim.2017, 53, 942.]

  14. Kopchuk, D. S.; Chepchugov, N. V.; Taniya, O. S.; Khasanov, A. F.; Giri, K.; Kovalev, I. S.; Santra, S.; Zyryanov, G. V.; Majee, A.; Rusinov, V. L.; Chupakhin, O. N. Tetrahedron Lett. 2016, 57, 5639.

    Article  CAS  Google Scholar 

  15. Kopchuk, D. S.; Nikonov, I. L.; Khasanov, A. F.; Giri, K.; Santra, S.; Kovalev, I. S.; Nosova, E. V.; Gundala, S.; Venkatapuram, P.; Zyryanov, G. V.; Majee, A.; Chupakhin, O. N. Org. Biomol. Chem. 2018, 16, 5119.

    Article  CAS  Google Scholar 

  16. Kopchuk, D. S.; Chepchugov, N. V.; Gorbunov, E. B.; Zyryanov, G. V.; Kovalev, I. S.; Nosova, E. V.; Slepukhin, P. A.; Rusinov, V. L.; Chupakhin, O. N. J. Iran. Chem. Soc. 2017, 14, 1507.

    Article  CAS  Google Scholar 

  17. Gonsalves, A. M. d’A. R.; Pinho e Melo, T. M. V. D.; Gilchrist, T. L. Tetrahedron1992, 48, 6821.

  18. Dhar, R.; Hühnermann, W.; Kämpchen, T.; Overheu, W.; Seitz, G. Chem. Ber. 1983, 116, 97.

    Article  CAS  Google Scholar 

  19. Himmelsbach, F.; Langkopf, E.; Eckhardt, M.; Maier, R.; Mark, M.; Tadayyon, M.; Lotz, R. WO Patent 2004/041820 A1.

  20. Balog, J.; Riedl, Z.; Hajós, G.; Miskolczy, Z.; Biczók, L. ARKIVOC2012, (v), 109.

  21. (a) Metal Free C–H Functionalization of Aromatics; Charushin, V. N.; Chupakhin, O. N., Eds.; Springer International Publishing: Cham, 2014, p. 283. a Chupakhin, O. N.; Charushin, V. N. Tetrahedron Lett. 2016, 57, 2665. b Chupakhin, O. N.; Charushin, V. N. Pure Appl. Chem. 2017, 89, 1195. c Chupakhin, O. N.; Postovskii, I. Ya. Russ. Chem. Rev.1976, 45, 454. [Usp. Khim.1976, 45, 908.]

  22. Konno, S.; Sagi, M.; Takaharu, E.; Fujimura, S.; Hayashi, K.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1721.

    Article  CAS  Google Scholar 

  23. Krinochkin, A. P.; Kopchuk, D. S.; Kovalev, I. S.; Zyryanov, G. V.; Rusinov, V. L.; Chupakhin, O. N. Russ. J. Org. Chem. 2019, 55, 266. [Zh. Org. Khim.2019, 55, 303.]

  24. Kozhevnikov, D. N.; Kovalev, I. S.; Prokhorov, A. M.; Rusinov, V. L.; Chupakhin O. N. Russ. Chem. Bull., Int. Ed.2003, 52, 1588. [Izv. Akad. Nauk, Ser. Khim.2003, 1504.]

  25. Prokhorov, A. M.; Mąkosza, M.; Chupakhin O. N. Tetrahedron Lett. 2009, 50, 1444.

    Article  CAS  Google Scholar 

  26. Kozhevnikov, D. N.; Kozhevnikov, V. N.; Kovalev, I. S.; Rusinov, V. L.; Chupakhin, O. N.; Aleksandrov, G. G. Russ. J. Org. Chem. 2002, 38, 744. [Zh. Org. Khim.2002, 38, 780.]

  27. Dubovtsev, A. Yu.; Dar'in, D. V.; Krasavin, M.; Kukushkin, V. Yu. Eur. J. Org. Chem. 2019, 1856.

  28. Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron1977, 33, 1043.

    Article  CAS  Google Scholar 

  29. Kozhevnikov, V. N.; Shabunina, O. V.; Kopchuk, D. S.; Ustinova, M. M.; König B.; Kozhevnikov, D. N. Tetrahedron2008, 64, 8963.

    Article  CAS  Google Scholar 

  30. (a) Kopchuk, D. S.; Khasanov, A. F.; Kovalev, I. S.; Zyryanov, G. V.; Rusinov, V. L.; Chupakhin, O. N. Mendeleev Commun. 2013, 23, 209. (b) Kopchuk, D. S.; Khasanov, A. F.; Krinochkin, A. P.; Kovalev, I. S.; Zyryanov, G. V.; Rusinov, V. L.; Chupakhin, O. N. Russ. J. Org. Chem. 2016, 52, 1036. [Zh. Org. Khim.2016, 52, 1041.] (с) Kopchuk, D. S.; Khasanov, A. F.; Chepchugov, N. V.; Kovalev, I. S.; Zyryanov, G. V.; Rusinov, V. L.; Chupakhin, O. N. Russ. J. Org. Chem. 2017, 53, 99. [Zh. Org. Khim.2017, 53, 103.]

  31. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr.2008, A64, 112.

    Article  Google Scholar 

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This work was supported by the Russian Science Foundation (grant 18-13-00365).

Elemental analysis was performed by the elemental analysis group of the Postovsky Institute of Organic Synthesis.

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Correspondence to Grigory V. Zyryanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(10), 978–984

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Kopchuk, D.S., Nikonov, I.L., Khasanov, A.F. et al. One-step synthesis of 1,4-bis(het)arylisoquinolines by the reaction of 1,2,4-triazines with arynes. Chem Heterocycl Comp 55, 978–984 (2019). https://doi.org/10.1007/s10593-019-02565-8

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