Везде

RAS PresidiumДоклады Российской академии наук. Химия, науки о материалах Doklady Chemistry

  • ISSN (Print) 2686-9535
  • ISSN (Online) 3034-5111

CATALYTIC SYNTHESIS OF NEW ALLYL-SUBSTITUTED TETRAOXAZACANES AND HEXAOXAZACANES

You can
PII
S3034511125060024-1
DOI
10.7868/S3034511125060024
Publication type
Article
Status
Published
Authors
N. N. Makhmudiyarova
  • Occupation: Senior Researcher, Laboratory of Heteroatomic Compounds
  • Affiliation: Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences
I. R. Ishmukhametova
  • Occupation: Junior Researcher, Laboratory of Heteroatomic Compounds
  • Affiliation: Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences
G.R. Zakarieva
  • Occupation: Postgraduate Student, Laboratory of Heteroatomic Compounds
  • Affiliation: Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences
T.V. Tyumkina
  • Occupation: Senior Researcher, Laboratory of Structural Сhemistry
  • Affiliation: Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences
U. M. Dzhemilev
  • Occupation: Corresponding Member of the RAS; Chief Researcher, Laboratory of Carbene Chemistry and Other Unstable Molecules
  • Affiliation: N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Volume/ Edition
Volume 525 / Issue number 1
Pages
27-36
Abstract
A highly selective method for the synthesis of N-allyl-tetraoxazocanes based on the Sm(III)-catalyzed recyclization of pentaoxaspiroalkanes with allylamine has been developed for the first time. A new reaction pathway for heptaoxadispiroalkanes has been established, which, under Sm(III) catalysis with allylamine, leads not to the expected recyclization but to selective cleavage with the formation of tetraoxazocanes and carbonyl compounds, expanding the understanding of the reactivity of polyperoxide systems. A method for the selective synthesis of previously inaccessible N-allyl-hexaoxazaspiroalkanes has been developed via the cycloaminomethylation of 1,1′-peroxybis(1-hydroperoxycycloalkanes) with 1,3,5-triallyl-1,3,5-triazinanone catalyzed by lanthanide complexes. A detailed comparative study of the conformational behavior of N-allyl derivatives has been conducted for the first time, showing a significant influence of the allyl substituent on the spatial organization and dynamics of the peroxide cycles, unlike their N-aryl analogs.
Keywords
катализ пентаоксаканы гептаоксадиспироалканы аллиламин рециклизация циклоаминометилирование 1,3,5-триаллил-1,3,5-триазинан N-аллил-тетраоксазаканы N-аллил-гексаоксазаканы цитотоксическая активность
Date of publication
01.01.2026
Year of publication
2026
Number of purchasers
0
Views
49

References

  1. 1. Coghi P., Yaremenko I.A., Prommana P., Wu J.N., Zhang R.L., Ng J.P.L., Belyakova Yu.Yu., Law B.Y.K., Radulov P.S., Uthaipibull C., Wong V.K.W., Terent’ev A.O. ChemMedChem. 2022. V. 17. P. e202200328. https://doi.org/10.1002/cmdc.202200328
  2. 2. Bu M., Yang B.B., Hu L. Curr. Med. Chem. 2016. V. 23. P. 383–405. http://dx.doi.org/10.2174/0929867323666151127200949
  3. 3. Liao L. Nat. Med. 2011. V. 17. P. 1217–1220. https://doi.org/10.1038/nm.2471
  4. 4. Tu Y. Chem. Rev. 2017. V. 117. P. 13806–13817. https://doi.org/10.1021/acs.chemrev.7b00176
  5. 5. Klayman D.L. Science. 1985. V. 228. P. 1049−1055. https://doi.org/10.1126/science.3887571
  6. 6. Butler A.R., Wu Y.-L. Chem. Soc. Rev. 1992. V. 21. P. 85−90. https://doi.org/10.1039/CS9922100085
  7. 7. Li Y., Wu Y.L. Curr. Med. Chem. 2003. V. 10. P. 2197−2230. https://doi.org/10.2174/0929867033456710
  8. 8. Hu X., Maimone T.J. J. Am. Chem. Soc. 2014. V. 136. P. 5287−5290. https://doi.org/10.1021/ja502208z
  9. 9. Feng Y., Holte D., Zoller J., Umemiya S., Simke L.R., Baran P.S. J. Am. Chem. Soc. 2015. V. 137. P. 10160−10163. https://doi.org/10.1021/jacs.5b07154
  10. 10. Cole R., Kirksey J., Moore J., Blankenship B., Diener U., Davis N. Appl. Microbiol. 1972. V. 24. P. 248–250. https://doi.org/10.1128/am.24.2.248-250.1972
  11. 11. Vangapandu S., Jain M., Kaur K., Patil P., Patel S.R., Jain R. Med. Res. Rev. 2007. V. 27. № 1. P. 65–107. https://doi.org/10.1002/med.20062
  12. 12. White N.J. Science. 2008. V. 320. P. 330–334. https://doi.org/10.1126/science.1155165
  13. 13. Nagelschmitz J., Voith B., Wensing G., Roemer A., Fugmann B., Haynes R.K., Kotecka B.M., Rieckmann K.H., Edstein M.D. Antimicrob. Agents Chemother. 2008. V. 52. № 9. P. 3085–3091. https://doi.org/10.1128/aac.01585-07
  14. 14. Sinclair D., Donegan S., Isba R., Lalloo D.G. Cochrane Database Syst. Rev. 2012. V. 6. Art. CD005967. https://doi.org/10.1002/14651858.cd005967.pub4
  15. 15. Hou J., Wang D., Zhang R., Wang H. Clin. Cancer Res. 2008. V. 14. P. 5519−5530. https://doi.org/10.1158/1078-0432.ccr-08-0197
  16. 16. Belyakova Yu.Yu., Radulov P.S., Novikov R.A., Prolomov I.V., Krivoshchapov N.V., Medvedev M.G., Yaremenko I.A., Alabugin I.V., Terent’ev A.O. J. Am. Chem. Soc. 2025. V. 147. P. 965−977. https://doi.org/10.1021/jacs.4c14062
  17. 17. Coghi P., Yaremenko I.A., Prommana P., Nasim A.A., Belyakova Yu.Yu., Chen R., Radulov P.S., Uthaipibull C., Terent’ev A.O., Wong V.K.W. ChemMedChem. 2025. V. 20. P. e202500181. https://doi.org/10.1002/cmdc.202500181
  18. 18. Yaremenko I.A., Belyakova Yu.Yu., Radulov P.S., Novikov R.A., Medvedev M.G., Krivoshchapov N.V., Korlyukov A.A., Alabugin I.V., Terent’ev A.O. J. Am. Chem. Soc. 2021. V. 143. P. 6634−6648. https://doi.org/10.1021/jacs.1c02249
  19. 19. Yaremenko I.A., Belyakova Yu.Yu., Radulov P.S., Novikov R.A., Medvedev M.G., Krivoshchapov N.V., Alabugin I.V., Terent’ev A.O. Org. Lett. 2022. V. 24. P. 6582−6587. https://doi.org/10.1021/acs.orglett.2c02551
  20. 20. Yaremenko I.A., Belyakova Yu.Yu., Radulov P.S., Novikov R.A., Medvedev M.G., Krivoshchapov N.V., Korlyukov A.A., Alabugin I.V., Terent′ev A.O. J. Am. Chem. Soc. 2022. V. 144. P. 7264−7282. https://doi.org/10.1021/jacs.2c00406
  21. 21. Yaremenko I.A., Belyakova Yu.Yu., Radulov P.S., Medvedev M.G., Krivoshchapov N.V., Alabugin I.V., Terent’ev A.O. J. Org. Chem. 2023. V. 88. P. 13782−13795. https://doi.org/10.1021/acs.joc.3c01415
  22. 22. Tyumkina T.V., Makhmudiyarova N.N., Kiyamutdinova G.M., Meshcheryakova E.S., Bikmukhametov K.Sh., Abdullin M.F., Khalilov L.M., Ibragimov A.G., Dzhemilev U.M. Tetrahedron. 2018. V. 74. P. 1749−1758. https://doi.org/10.1016/j.tet.2018.01.045
  23. 23. Makhmudiyarova N.N., Ishmukhametova I.R., Dzhemileva L.U., Tyumkina T.V., D’yakonov V.A., Ibragimov A.G., Dzhemilev U.M. RSC Adv. 2019. V. 9. P. 18923−18929. https://doi.org/10.1039/C9RA02950H
  24. 24. Makhmudiyarova N.N., Ishmukhametova I.R., Tyumkina T.V., Mescheryakova E.S., Dzhemileva L.U., D’yakonov V.A., Terent’ev A.O., Dzhemilev U.M. J. Org. Chem. 2023. V. 88. P. 11473−11485. https://doi.org/10.1021/acs.joc.3c00555
  25. 25. Makhmudiyarova N.N., Khatmullina G.M., Rakhimov R.Sh., Meshcheryakova E.S., Ibragimov A.G., Dzhemilev U.M. Tetrahedron. 2016. V. 72. P. 3277−3281. https://doi.org/10.1016/j.tet.2016.04.055
  26. 26. Makhmudiyarova N.N., Ishmukhametova I.R., Tyumkina T.V., Ibragimov A.G., Dzhemilev U.M. Tetrahedron Lett. 2018. V. 59. P. 3161−3164. https://doi.org/10.1016/j.tetlet.2018.07.010/
  27. 27. Makhmudiyarova N.N., Ishmukhametova I.R., Dzhemileva L.U., D’yakonov V.A., Terent’ev A.O., Dzhemilev U.M. ChemistrySelect. 2023. V. 8. P. e202302044. https://doi.org/10.1002/slct.202302044
QR
Translate

Indexing

Scopus

Scopus

Scopus

Crossref

Scopus

Higher Attestation Commission

At the Ministry of Education and Science of the Russian Federation

Scopus

Scientific Electronic Library