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Synthesis of new photochromic diarylethenes of cyclopentenone series by Nazarov reaction

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Chemistry of Heterocyclic Compounds Aims and scope

An effective method is proposed for the synthesis of photochromic diarylethenes of cyclopentenone series with SnCl4-catalyzed 4π-electron cyclization of divinyl ketones by Nazarov reaction as the key step. It was shown that the introduction of an aryl group at position 4 of the cyclopentenone ring significantly improved the quantum yield of diarylethene photocyclization reaction.

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References

  1. Irie, M.; Fukaminato, T.; Matsuda, K.; Kobatake, S. Chem. Rev. 2014, 114, 12174.

    CAS  Google Scholar 

  2. Tsujioka, T.; Onishi, I.; Natsume, D. Appl. Opt. 2010, 49, 3894.

    Article  CAS  Google Scholar 

  3. Minkin, V. I. Russ. Chem. Bull. 2008, 57, 687. [Izv. Akad. Nauk, Ser. Khim. 2008, 673.]

    Article  CAS  Google Scholar 

  4. Orgiu, E.; Samorì, P. Adv. Mater. 2014, 26, 1827.

    Article  CAS  Google Scholar 

  5. Szymański, W.; Beierle, J. M.; Kistemaker, H. A. V.; Velema, W. A.; Feringa, B. L. Chem. Rev. 2013, 113, 6114.

    Article  Google Scholar 

  6. Zhang, J., Wang, J., Tian, H. Mater. Horiz. 2014, 1, 169.

    Article  CAS  Google Scholar 

  7. Shirinian, V. Z.; Lonshakov, D. V.; Lvov, A. G.; Krayushkin, M. M. Russ. Chem. Rev. 2013, 82, 511. [Usp. Khim. 2013, 82, 511.]

    Article  Google Scholar 

  8. Lonshakov, D. V.; Shirinian, V. Z.; Zavarzin, I. V.; Lvov, A. G.; Krayushkin, M. M. Dyes Pigm. 2014, 109, 105.

    Article  CAS  Google Scholar 

  9. Lonshakov, D. V.; Shirinian, V. Z.; Lvov, A. G.; Nabatov, B. V.; Krayushkin, M. M. Dyes Pigm. 2013, 97, 311.

    Article  CAS  Google Scholar 

  10. Shepelenko, E. N.; Makarova, N. I.; Karamov, O. G.; Dubonosov, A. D.; Podshibakin, V. A.; Metelitsa, A. V.; Bren', V. A.; Minkin, V. I. Chem. Heterocycl. Compd. 2014, 50, 932. [Khim. Geterotsikl. Soedin. 2014, 1013.]

    Article  CAS  Google Scholar 

  11. Makarova, N. I.; Shepelenko, E. N.; Karamov, O. G.; Metelitsa, A. V.; Bren', V. A.; Minkin, V. I. Russ. Chem. Bull. 2014, 63, 109. [Izv. Akad. Nauk, Ser. Khim. 2014, 109.]

    Article  CAS  Google Scholar 

  12. Nakamura, S.; Uchida, K.; Hatakeyama, M. Molecules 2013, 18, 5091.

    Article  CAS  Google Scholar 

  13. Morinaka, K.; Ubukata, T.; Yokoyama, Y. Org. Lett. 2009, 11, 3890.

    Article  CAS  Google Scholar 

  14. Fukumoto, S.; Nakashima, T.; Kawai, T. Angew. Chem., Int. Ed. 2011, 50, 1565.

    Article  CAS  Google Scholar 

  15. Ogawa, H.; Takagi, K.; Ubukata, T.; Okamoto, A.; Yonezawa, N.; Delbaere, S.; Yokoyama, Y. Chem. Commun. 2012, 48, 11838.

    Article  CAS  Google Scholar 

  16. Pu, S.; Zheng, C.; Sun, Q.; Liu, G.; Fan, C. Chem. Commun. 2013, 49, 8036.

    Article  CAS  Google Scholar 

  17. Shirinian, V. Z.; Lvov, A. G.; Krayushkin, M. M.; Lubuzh, E. D.; Nabatov, B. V. J. Org. Chem. 2014, 79, 3440.

    Article  CAS  Google Scholar 

  18. Göstl, R.; Kobin, B.; Grubert, L.; Patzel, M.; Hecht, S. Chem.–Eur. J. 2012, 18, 14282.

    Article  Google Scholar 

  19. Li, W.; Jiao, C.; Li, X.; Xie, Y.; Nakatani, K.; Tian, H.; Zhu, W. Angew. Chem., Int. Ed. 2014, 53, 4603.

    Article  CAS  Google Scholar 

  20. Shirinian, V. Z.; Shimkin, A. A.; Lonshakov, D. V.; Lvov, A. G.; Krayushkin, M. M. J. Photochem. Photobiol. A 2012, 233, 1.

    Article  CAS  Google Scholar 

  21. Shirinian, V. Z.; Lonshakov, D. V.; Kachala, V. V.; Zavarzin, I. V.; Shimkin, A. A.; Lvov, A. G.; Krayushkin, M. M. J. Org. Chem. 2012, 77, 8112.

    Article  CAS  Google Scholar 

  22. Shirinian, V. Z.; Lonshakov, D. V.; Lvov, A. G.; Shimkin, A. A.; Krayushkin, M. M. Photochem. Photobiol. Sci. 2013, 12, 1717.

    Article  CAS  Google Scholar 

  23. Lonshakov, D. V.; Shirinian, V. Z.; Lvov, A. G.; Krayushkin, M. M. Mendeleev Commun. 2013, 23, 268.

    Article  CAS  Google Scholar 

  24. Habermas, K. L.; Denmark, S. E.; Jones, T. D. In Organic Reactions, Paquette, L. A., Ed.; John Wiley & Sons, Inc., 1994, vol. 45, p. 1.

  25. Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577.

    Article  CAS  Google Scholar 

  26. Aggarwal, V. K.; Belfield, A. J. Org. Lett. 2003, 5, 5075.

    Article  CAS  Google Scholar 

  27. Kawatsura, M.; Kajita, K.; Hayase, S.; Itoh, T. Synlett 2010, 1243.

  28. He, W.; Sun, X. F.; Frontier, A. J. J. Am. Chem. Soc. 2003, 125, 14278.

    Article  CAS  Google Scholar 

  29. Mikhailov, I. E.; Dushenko, G. A.; Minkin, V. I. Molecular Rearrangaments of Cyclopolyenes [in Russian]; Nauka, 2008, ch. III.2, p. 16 and ch. III.4, p. 19.

  30. Uchida, K.; Tsuchida, E.; Aoi, Y.; Nakamura, S.; Irie, M. Chem. Lett. 1999, 28, 63.

    Article  Google Scholar 

  31. Nakashima, H.; Irie, M. Macromol. Chem. Phys. 1999, 200, 683.

    Article  CAS  Google Scholar 

  32. Shimkin, A. A.; Shirinian, V. Z.; Mailian, A. K.; Lonshakov, A. G.; Gorokhov, V. V.; Krayushkin, M. M. Russ. Chem. Bull. 2011, 60, 139. [Izv. Akad. Nauk, Ser. Khim. 2011, 134.]

    Article  CAS  Google Scholar 

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The work was performed with financial support from the Russian Foundation for Basic Research (grant 14-03-31871).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Valerii Z. Shirinian, Andrey G. Lvov, Vadim V. Kachala & Mikhail Krayushkin

  2. D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow, 125047, Russia

    Anna M. Yanina

Authors
  1. Valerii Z. Shirinian
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  2. Andrey G. Lvov
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  3. Anna M. Yanina
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  4. Vadim V. Kachala
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  5. Mikhail Krayushkin
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Correspondence to Valerii Z. Shirinian.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(3), 234–241

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Shirinian, V.Z., Lvov, A.G., Yanina, A.M. et al. Synthesis of new photochromic diarylethenes of cyclopentenone series by Nazarov reaction. Chem Heterocycl Comp 51, 234–241 (2015). https://doi.org/10.1007/s10593-015-1690-9

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  • DOI: https://doi.org/10.1007/s10593-015-1690-9

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