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Catalytic synthesis of spiromacrocyclic diperoxides based on α,ω-diols

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Abstract

Cyclocondensation reaction of linear α,ω-diols (C3, C5, C6, and C8) with 1,1-dihydroperoxycycloalkanes and formaldehyde with the participation of lanthanide catalysts affords spiromacrocyclic diperoxides.

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References

  1. D. A. Casteel, Nat. Prod. Rep., 1992, 9, 289; DOI: https://doi.org/10.1039/NP9920900289.

    Article  CAS  PubMed  Google Scholar 

  2. K. J. McCullough, M. Nojima, Curr. Org. Chem., 2001, 5, 601; DOI: https://doi.org/10.2174/1385272013375346.

    Article  CAS  Google Scholar 

  3. D. A. Casteel, Nat. Prod. Rep., 1999, 16, 55; DOI: https://doi.org/10.1039/A705725C.

    Article  Google Scholar 

  4. M. Bu, B. B. Yang, L. Hu, Curr. Med. Chem., 2016, 23, 383; DOI: https://doi.org/10.2174/0929867323666151127200949.

    Article  CAS  PubMed  Google Scholar 

  5. A. Robert, R. A. Meunier, Chem. Soc. Rev., 1998, 27, 273; DOI: https://doi.org/10.1039/A827273Z.

    Article  CAS  Google Scholar 

  6. J. L. Vennerstrom, H.-N. Fu, W. Y. Ellis, Jr. A. L. Ager, J. K. Wood, S. L. Andersen, L. Gerena, W. K. Milhous, J. Med. Chem., 1992, 35, 3023; DOI: https://doi.org/10.1039/A900826H.

    Article  CAS  PubMed  Google Scholar 

  7. G. H. Posner, H. O’Dowd, T. Caferro, J. N. Cumming, P. Ploypradith, S. Xie, T. A. Shapiro, Tetrahedron Lett., 1998, 39, 2273–2276; DOI: https://doi.org/10.1016/S0040-4039(98)00290-1.

    Article  CAS  Google Scholar 

  8. P. H. Dussault, K. Woller, J. Am. Chem. Soc., 1997, 119, 3824–3825; DOI: https://doi.org/10.1021/ja970174p.

    Article  CAS  Google Scholar 

  9. P. M. O’Neill, N. L. Searle, K. J. Raynes, J. L. Maggs, S. A. Ward, R. C. Storr, B. K. Park, G. H. Posner, Tetrahedron Lett., 1998, 39, 6065–6068; DOI: https://doi.org/10.1016/S0040-4039(98)01248-9.

    Article  Google Scholar 

  10. S. Fielder, D. D. Rowan, M. S. Sherburn, Tetrahedron., 1998, 54, 12907–12922; DOI: https://doi.org/10.1016/S0040-4020(98)00782-0.

    Article  CAS  Google Scholar 

  11. H.-S. Kim, Y. Nagai, K. Ono, K. Begum, Y. Wataya, Y. Hamada, K. Tsuchiya, A. Masuyama, M. Nojima, K. McCullough, J. Med. Chem., 2001, 44, 2357–2361; DOI: https://doi.org/10.1021/jm010026g.

    Article  CAS  PubMed  Google Scholar 

  12. K. J. McCullough, T. Ito, T. Tokuyasu, A. Masuyama, M. Nojima, Tetrahedron Lett., 2001, 42, 5529–5532; DOI: https://doi.org/10.1016/S0040-4039(01)01015-2.

    Article  CAS  Google Scholar 

  13. T. Ito, T. Tokuyasu, A. Masuyama, M. Nojimaa, K. J. McCullough, Tetrahedron, 2003, 59, 525–536; DOI: https://doi.org/10.1016/S0040-4020(02)01556-9.

    Article  CAS  Google Scholar 

  14. K. J. McCullough, H. Tokuhara, A. Masuyama, M. Nojima, Org. Biomol. Chem., 2003, 1, 1522–1527; DOI: https://doi.org/10.1039/B300342F.

    Article  CAS  PubMed  Google Scholar 

  15. Y. Nonami, Y. Ushigoe, A. Masuyama, M. Nojima, K. J. McCullough, Tetrahedron Lett., 1998, 39, 6597–6600; DOI: https://doi.org/10.1016/S0040-4039(98)01375-6.

    Article  CAS  Google Scholar 

  16. K. J. McCullough, Y. Nonami, A. Masuyama, M. Nojima, H.-S. Kim, Y. Wataya, Tetrahedron Lett., 1999, 40, 9151–9155; DOI: https://doi.org/10.1016/S0040-4039(99)01944-9.

    Article  CAS  Google Scholar 

  17. A. V. Arzumanyan, R. A. Novikov, A. O. Terent’ev, M. M. Platonov, V. G. Lakhtin, D. E. Arkhipov, A. A. Korlyukov, V. V. Chernyshev, A. N. Fitch, A. T. Zdvizhkov, I. B. Krylov, Y. V. Tomilov, G. I. Nikishin, Organometallics, 2014, 33, 2230–2246; DOI: https://doi.org/10.1021/om500095x.

    Article  CAS  Google Scholar 

  18. A. V. Arzumanyan, A. O. Terent’ev, R. A. Novikov, V. G. Lakhtin, V. V. Chernyshev, A. N. Fitch, G. I. Nikishin, Eur. J. Org. Chem., 2014, 31, 6877–6883; DOI: https://doi.org/10.1002/ejoc.201402895.

    Article  Google Scholar 

  19. N. N. Makhmudiyarova, I. R. Ishmukhametova, T. V. Tyumkina, A. G. Ibragimov, U. M. Dzhemilev, Tetrahedron Lett., 2018, 59, 3161–3164; DOI: https://doi.org/10.1016/j.tetlet.2018.07.010.

    Article  CAS  Google Scholar 

  20. N. N. Makhmudiyarova, G. M. Khatmullina, R. Sh. Rakhimov, E. S. Meshcheryakova, A. G. Ibragimov, U. M. Dzhemilev, Tetrahedron, 2016, 72, 3277–3281; DOI: https://doi.org/10.1016/j.tet.2016.04.055.

    Article  CAS  Google Scholar 

  21. N. N. Makhmudiyarova, I. R. Ishmukhametova, L. U. Dzhemileva, T. V. Tyumkina, V. A. D’yakonov, A. G. Ibragimov, U. M. Dzhemilev, RSC Adv., 2019, 9, 18923–18929; DOI: https://doi.org/10.1039/C9RA02950H.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. N. N. Makhmudiyarova, I. R. Ishmukhametova, L. U. Dzhemileva, V. A. D’yakonov, A. G. Ibragimov, U. M. Dzhemilev, Molecules, 2020, 25, 1874; DOI: https://doi.org/10.3390/molecules25081874.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. N. N. Makhmudiyarova, I. R. Ishmukhametova, A. G. Ibragimov, U. M. Dhzemilev, Dokl. Chem., 2020, 492, 93–100; DOI: https://doi.org/10.31857/S2686953520040044.

    Article  CAS  Google Scholar 

  24. I. Ugi, S. Heck, Comb. Chem. High Throughput Screen., 2001, 4, 1–34; DOI: https://doi.org/10.2174/1386207013331291.

    Article  CAS  PubMed  Google Scholar 

  25. P. A. Grieco, A. Bahsas, Tetrahedron Lett., 1988, 29, 5855–5858; DOI: https://doi.org/10.1016/S0040-4039(00)82208-X.

    Article  CAS  Google Scholar 

  26. B. M. Trost, Science, 1991, 254, 1471–1477; DOI: https://doi.org/10.1126/science.1962206.

    Article  CAS  PubMed  Google Scholar 

  27. N. N. Makhmudiyarova, I. R. Ishmukhametova, K. R. Shangaraev, L. U. Dzhemileva, V. A. D’yakonov, A. G. Ibragimov, U. M. Dzhemilev, N. J. Chem., 2021, 45, 2069–2077; DOI: https://doi.org/10.1039/D0NJ05511E.

    Article  CAS  Google Scholar 

  28. S. Oda, J. Franke, M. Krishce, J. Chem. Sci., 2016, 7, 136–141; DOI: https://doi.org/10.1039/C5SC03854E.

    CAS  Google Scholar 

  29. U. Wellmar, J. Heterocycl. Chem., 1998, 35, 1531–1532; DOI: https://doi.org/10.1002/jhet.5570350653.

    Article  CAS  Google Scholar 

  30. K. Krohn, S. Cludius-Brandt, Synthesis, 2010, 8, 1344–1348; DOI: https://doi.org/10.1055/s-0029-1218658.

    Article  Google Scholar 

  31. S. Vojacek, K. Beese, Z. Alhalabi, S. Swyter, A. Bodtke, C. Carola Schulzke, M. Jung, W. Sippl, A. Link, Arch. Pharm., 2017, 350, e1700097; DOI: https://doi.org/10.1002/ardp.201700097.

    Article  Google Scholar 

  32. H. Liangjie, W. Dan, X. Weilan, C. Jing, Z. Zuoxiang, China Pat. CN102086203 A; 2011.

  33. A. O. Terent’ev, M. M. Platonov, Y. N. Ogibin, G. I. Nikishin, Synthetic Commun., 2007, 37, 1281–1287; DOI: https://doi.org/10.1080/00397910701226384.

    Article  Google Scholar 

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Correspondence to N. N. Mahmudiyarova.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

The study was financially supported by the Russian Foundation for Basic Research (Project No. 22-13-00202). Synthesis of 12-membered macrocyclic diperoxides was carried out as a part of the state task of the Ministry of Science and Higher Education of the Russian Federation (No. FMRS-2022-0079).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1161–1165, May, 2023.

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Mahmudiyarova, N.N., Ishmukhametova, I.R. & Dzhemilev, U.M. Catalytic synthesis of spiromacrocyclic diperoxides based on α,ω-diols. Russ Chem Bull 72, 1161–1165 (2023). https://doi.org/10.1007/s11172-023-3884-0

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  • DOI: https://doi.org/10.1007/s11172-023-3884-0

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