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Efficient one-step synthesis of 3-aryl-2-pyridones from 6-aryl-1,2,4-triazin-5-ones

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Chemistry of Heterocyclic Compounds Aims and scope

An efficient method for the synthesis of substituted 2-pyridones based on the aza-Diels–Alder reaction of 1,2,4-triazin-5-ones and dienophiles, 2,5-norbornadiene and 4-(cyclopent-1-en-1-yl)morpholine, is proposed.

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References

  1. (а) Schultz, A. G. Chem. Rev.1973, 73, 385. a Teshima, Y.; Shin-Ya, K.; Shimazu, A.; Furihata, K.; Chul, H. S.; Furihata, K.; Hayakawa, Y.; Nagai, K.; Seto, H. J. Antibiot.1991, 44, 685.

  2. Chong, D. J.; Lerman, A. M. Curr. Neurol. Neurosci. Rep.2016, 16, 39.

    Article  Google Scholar 

  3. Niewerth, M.; Kunze, D.; Seibold, M.; Schaller, M.; Korting, H. C.; Hube, B. Antimicrob. Agents Chemother.2003, 47, 1805.

    Article  CAS  Google Scholar 

  4. Koster, G.; Bekema, H. J.; Wetterslev, J.; Gluud, C.; Keus, F.; van der Horst, I. C. C. Intensive Care Med.2016, 42, 1322.

    Article  CAS  Google Scholar 

  5. Wu, B.; Oesker, V.; Wiese, J.; Schmaljohann, R.; Imhoff, J. F. Mar. Drugs2014, 12, 1208.

    Article  CAS  Google Scholar 

  6. (a) Morimoto, K.; Furusawa, H.; Terachi, T.; Nawamaki, T.; Watanabe, S.; Nakahira, K.; Noguchi, J. WO Patent 9857957; Chem. Abstr.1999, 130, 66511b. (b) TePaske, M. R.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. Tetrahedron Lett.1991, 32, 5687.

  7. Sellstedt, M.; Nyberg, A.; Rosenbaum, E.; Engström, P.; Wickström, M.; Gullbo, J.; Bergström, S.; Johansson, L. B.-Å; Almqvist, F. Eur. J. Org. Chem.2010, 6171.

  8. Hagimori, M.; Mizuyama, N.; Tominaga, Y.; Mukai, T.; Saji, H. Dyes Pigm.2015, 113, 205.

    Article  CAS  Google Scholar 

  9. Mizuyama, N.; Tominaga, Y.; Kohra, S.; Ueda, K.; Hirayama, S.; Shigemitsu, Y. Bull. Chem. Soc. Jpn. 2006, 79, 602.

    Article  CAS  Google Scholar 

  10. (а) Torres, M.; Gil, S.; Parra, M. Curr. Org. Chem.2005, 9, 1757. a Heravi, M. M.; Hamidi, H. J. Iran. Chem. Soc.2013, 10, 265. b Hamama, W. S.; Waly, M.; El-Hawary, I.; Zoorob, H. H. Synth. Commun.2014, 44, 1730.

  11. (а) Pabst, G. R.; Sauer, J. Tetrahedron Lett.1998, 39, 6687. a Rykowski, A.; Branowska, D.; Kielak, J. Tetrahedron Lett.2000, 41, 3657. b Kozhevnikov, V. N.; Shabunina, O. V.; Kopchuk, D. S.; Ustinova, M. M.; König, B.; Kozhevnikov, D. N. Tetrahedron2008, 64, 8963. c 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.

  12. Taylor, E. C. Bull. Soc. Chim. Belg.1988, 97, 599.

    Article  CAS  Google Scholar 

  13. (a) Taylor, E. C.; Pont, J. L.; Warner, J. C. J. Heterocycl. Chem.1988, 25, 1733. (b) Taylor, E. C.; Pont, J. L.; Van Engen, D.; Warner, J. C. J. Org. Chem.1988, 53, 5093.

  14. Savchuk, M. I.; Starnovskaya, E. S.; Shtaitz, Y. K.; Kopchuk, D. S.; Nosova, E. V.; Zyryanov, G. V.; Rusinov, V. L.; Chupakhin, O. N. Russ. J. Gen. Chem.2018, 88, 2213. [Zh. Obshch. Khim.2018, 88, 1728.]

  15. Shtaitz, Ya. K.; Savchuk, M. I.; Starnovskaya, E. S.; Krinochkin, A. P.; Kopchuk, D. S.; Santra, S.; Zyryanov, G. V.; Rusinov, V. L.; Chupakhin, O. N. AIP Conf. Proc.2019, 2063, 040050.

    Article  Google Scholar 

  16. Fatykhov, R. F.; Savchuk, M. I.; Starnovskaya, E. S.; Bobkina, M. V.; Kopchuk, D. S.; Nosova, E. V.; Zyryanov, G. V.; Khalymbadzha, I. A.; Chupakhin, O. N.; Charushin, V. N.; Kartsev, V. G. Mendeleev Commun.2019, 29, 299.

    Article  CAS  Google Scholar 

  17. (a) Kozhevnikov, V. N.; Kozhevnikov, D. N.; Nikitina, T. V.; Rusinov, V. L.; Chupakhin, O. N.; Zabel, M.; König, B. J. Org. Chem.2003, 68, 2882. (b) 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.]

  18. (a) Rykowski, A.; Branowska, D.; Makosza, M.; Van Ly, P. J. Heterocycl. Chem.1996, 33, 1567. (b) Huang, J. J. J. Org. Chem.1985, 50, 2293. (c) Kozhevnikov, V. N.; Cowling, S. J.; Karadakov, P. B.; Bruce, D. W. J. Mater. Chem.2008, 18, 1703. (d) Chupakhin, O. N.; Egorov, I. N.; Rusinov, V. L.; Slepukhin, P. A. Russ. Chem. Bull., Int. Ed.2010, 59, 991. [Izv. Akad. Nauk, Ser. Khim.2010, 970.]

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

    Article  CAS  Google Scholar 

  20. Chauhan, P.; Ravi, M.; Singh, S.; Prajapati, P.; Yadav, P. P. RSC Adv.2016, 6, 109.

    Article  CAS  Google Scholar 

  21. Neunhoeffer, H.; Reichel, D.; Cullmann, B.; Rehn, I. Liebigs Ann. Chem.1990, 631.

    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 an elemental analysis group of the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences.

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Authors and Affiliations

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

    Maria I. Savchuk, Yaroslav K. Shtaitz, Dmitry S. Kopchuk, Grigory V. Zyryanov, Oleg S. Eltsov, Tatiana А. Pospelova, Vladimir L. Rusinov & Oleg N. Chupakhin

  2. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 21 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg, 620219, Russia

    Dmitry S. Kopchuk, Grigory V. Zyryanov, Vladimir L. Rusinov & Oleg N. Chupakhin

Authors
  1. Maria I. Savchuk
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  2. Yaroslav K. Shtaitz
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  3. Dmitry S. Kopchuk
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  4. Grigory V. Zyryanov
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  5. Oleg S. Eltsov
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  6. Tatiana А. Pospelova
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  7. Vladimir L. Rusinov
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  8. Oleg N. Chupakhin
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Corresponding author

Correspondence to Grigory V. Zyryanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(10), 985–988

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Savchuk, M.I., Shtaitz, Y.K., Kopchuk, D.S. et al. Efficient one-step synthesis of 3-aryl-2-pyridones from 6-aryl-1,2,4-triazin-5-ones. Chem Heterocycl Comp 55, 985–988 (2019). https://doi.org/10.1007/s10593-019-02566-7

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