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Synthesis of unsymmetrical cage phosphonates from heterocyclic systems based on 2H-1,2-benzoxaphosphinine

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Chemistry of Heterocyclic Compounds Aims and scope

It was found that the reaction of 2-hydroxy-5,7,8-trimethyl-2H-1,2-benzoxaphosphinine 2-oxide with resorcinol and its derivatives as well as sesamol leads to the formation of phosphaneoflavanones in high yields. The obtained phosphaneoflavanones are precursors in the synthesis of novel unsymmetrical cage phosphonates. The structures of the obtained products were confirmed by IR spectroscopy, 1H, 13C NMR spectroscopy, and X-ray structural analysis.

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References

  1. Coumarins: Biology, Applications and Mode of Action; O’Kennedy, R.; Thornes, R. D., Eds; Wiley: Chichester, 1997.

  2. Kostova, I. Curr. Med. Chem.: Anti-Cancer Agents 2005, 5, 29.

  3. Sabry, N. M.; Mohamed, H. M.; Khattab, Essam Shawky A. E. H.; Motlaq, S. S.; El-Agrody, A. M. Eur. J. Med. Chem. 2011, 46, 765.

  4. Anand, P.; Singh, B.; Singh, N. Bioorg. Med. Chem. 2012, 20, 1175.

  5. Cardoso, S. H.; Barreto, M. B.; Lourenço, M. C. S.; Henriques, M. d. G. M. d. O.; Candéa, A. L. P.; Kaiser, C. R.; de Souza, M. V. N. Chem. Biol. Drug Des. 2011, 77, 489.

  6. Li , X.; Wang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Bioorg. Chem. 2006, 34, 105.

  7. Grazul, M; Budzisz, E. Coord. Chem. Rev. 2009, 253, 2588.

  8. Budzisz, E. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 2131.

  9. Son, J-Yu; Kim, H.; Jeon, W. H.; Baek, Y.; Seo, B.; Um, K.; Lee, K.; Lee, P.H. Adv. Synth. Catal. 2017, 359, 3194.

    Article  CAS  Google Scholar 

  10. Unoh, Y.; Hashimoto, Y.; Takeda, D.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2013, 15, 3258.

    Article  CAS  Google Scholar 

  11. Kim, C-E.; Ryu, T.; Kim, S.; Lee, K.; Lee, C.-H.; Lee, P.H. Adv. Synth. Catal. 2013, 355, 2873.

    Article  CAS  Google Scholar 

  12. Ryzhkina, I. S.; Murtazina, L. I.; Nemtarev, A. V.; Mironov, V. F.; Konovalov, A. I. Mendeleev Commun. 2010, 20, 148.

    Article  CAS  Google Scholar 

  13. Bochkova, O. D.; Mustafina, A. R.; Mukhametshina, A. R.; Burilov, V. A.; Nemtarev, A.V.; Mironov, V. F.; Konovalov, A. I. Talanta 2012, 93, 233.

    Article  CAS  Google Scholar 

  14. Kim, C.-E.; Son, J.-Y.; Shin, S.; Seo, B.; Lee, P. H. Org. Lett. 2015, 17, 908.

    Article  CAS  Google Scholar 

  15. Tatarinov, D. A.; Kuznetsov, D. M.; Fayzullin, R. R.; Mironov, V. F. J. Organomet. Chem. 2020, 918, 121313.

    Article  CAS  Google Scholar 

  16. Sadykova, Y. M.; Dalmatova, N. V.; Voronina, Y. K.; Burilov, A. R.; Pudovik, M. A.; Sinyashin, O. G. Heteroat. Chem. 2012, 23, 340.

    Article  CAS  Google Scholar 

  17. Sadykova, Yu. M.; Sadikova, L. M.; Badrtdinova, A. R.; Dobrynin, A. B.; Burilov, A. R.; Pudovik, M. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 2267.

  18. Babouri, R.; Traore, L.; Bekro, Y.-A.; Matveeva, V. I.; Sadykova, Y. M.; Voronina, J. K.; Burilov, A. R.; Ayad, T.; Volle, J.-N.; Virieux, D.; Pirat, J.-L. Org. Lett. 2019, 21, 45.

    Article  CAS  Google Scholar 

  19. Sadykova, Y. M.; Sadikova, L. M.; Zalaltdinova, A. V.; Strelnik, A. G.; Burilov, A. R.; Pudovik, M. Mendeleev Commun. 2018, 28, 655.

    Article  CAS  Google Scholar 

  20. Sheldrick, G. M. SHELXTL v. 6.12, Structure Determination Software Suit; Bruker AXS: Madison, 2000.

  21. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

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The study was carried out with the financial support of the Russian Foundation for Basic Research within the framework of the scientific project 20-03-00118.

The authors are grateful to the Collective Spectro-Analytical Center for Physicochemical Studies of the Structure, Properties and Composition of Substances and Materials of Kazan Scientific Center, Russian Academy of Sciences for technical support of the studies. X-ray structural analysis was performed using the equipment of the Center for Collective Use of Physical Methods for the Study of Substances and Materials of Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, which functions with the support of the State Assignment to Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences in the field of fundamental scientific research

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center, Russian Academy of Sciences, 8 Akademika Arbuzova St., Kazan, 420088, Russia

    Yulia M. Sadykova, Alexander R. Burilov & Mikhail A. Pudovik

  2. Kazan National Research Technological University, 68 Karla Marksa St., Kazan, 420015, Russia

    Alena V. Zalaltdinova & Atabek K. Smailov

  3. Chuvash State University named after I. N. Ulianov, 19 Moskovskiy Ave., Cheboksary, 428015, Russia

    Larisa M. Trofimova

  4. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky Ave., Moscow, 119991, Russia

    Julia K. Voronina

  5. Plekhanov Russian University of Economics, 36 Stremyanny Lane, Moscow, 117997, Russia

    Julia K. Voronina

Authors
  1. Yulia M. Sadykova
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  2. Alena V. Zalaltdinova
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  3. Atabek K. Smailov
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  4. Larisa M. Trofimova
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  5. Julia K. Voronina
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  6. Alexander R. Burilov
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  7. Mikhail A. Pudovik
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Corresponding author

Correspondence to Yulia M. Sadykova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(11), 1605–1610

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Sadykova, Y.M., Zalaltdinova, A.V., Smailov, A.K. et al. Synthesis of unsymmetrical cage phosphonates from heterocyclic systems based on 2H-1,2-benzoxaphosphinine. Chem Heterocycl Comp 56, 1605–1610 (2020). https://doi.org/10.1007/s10593-020-02856-5

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  • DOI: https://doi.org/10.1007/s10593-020-02856-5

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