Abstract
A promising method for the synthesis of a new class of macrocyclic phosphorus-containing tri- and diperoxides was developed. The method is based on catalytic ring transformation reactions of heptaoxadispiroalkanes, pentaoxacanes, and pentaoxadispiroalkanes with phenylphosphine followed by oxidation of the reaction mixture with H2O2.
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REFERENCES
Makhmudiyarova, N.N., Khatmullina, G.M., Rakhimov, R.Sh., et al., Tetrahedron, 2016, vol. 72, pp. 3277–3281. https://doi.org/10.1016/j.tet.2016.04.055
Makhmudiyarova, N.N., Ishmukhametova, I.R., Tyumkina, T.V., et al., Tetrahedron Lett., 2018, vol. 59, pp. 3161–3164. https://doi.org/10.1016/j.tetlet.2018.07.010
Makhmudiyarova, N.N., Ishmukhametova, I.R., Dzhemileva, L.U., et al., RSC Adv., 2019, vol. 9, pp. 18923–18929. https://doi.org/10.1039/C9RA02950H
Makhmudiyarova, N., Ishmukhametova, I., Dzhemileva, L., D’yakonov, V., Ibragimov, A., and Dzhemi-lev, U., Molecules, 2020, vol. 25, p. 1874. https://doi.org/10.3390/molecules25081874
Arzumanyan, A.V., Novikov, R.A., Terent’ev, A.O., et al., Organometallics, 2014, vol. 33, pp. 2230–2246. https://doi.org/10.1021/om500095x
Bartlett, P.D. and Lonzetta, C.M., J. Am. Chem. Soc., 1983, vol. 105, pp. 1984–1988. https://doi.org/10.1021/ja00345a054
Itzstein, M. and Jenkins, I.D., J. Chem. Soc., Chem. Commun., 1983, pp. 164–165. https://doi.org/10.1039/C19650000587
Ho, D.G., Gao, R., Celaje, J., et al., Science, 2003, vol. 302, pp. 259–263. https://doi.org/10.1126/science.1089145
Mardyukov, A., Niedek, D., and Schreiner, P.R., J. Am. Chem. Soc., 2017, vol. 139, no. 14, pp. 5019–5022. https://doi.org/10.1021/jacs.7b01639
Zhang, D., Gao, R., Afzal, S., et al., Org. Lett., 2006, vol. 8, pp. 5125–5128. https://doi.org/10.1021/ol0622007
Korth, H.-G. and Lommes, P., Chem. Ber., 1992, vol. 125, pp. 2419–2437. https://doi.org/10.1002/cber.19921251114
Sosnovsky, G. and Zaret, E.H., Org. Chem., 1969, vol. 34, pp. 968–970. https://doi.org/10.1021/jo01256a042
Klayman, D.L., ACS Symp. Ser., 1993, vol. 534, pp. 242–255. https://doi.org/10.1021/bk-1993-0534.ch017
Vil’, V.A., Yaremenko, I.A., Ilovaisky, A.I., and Terent’ev, A.O., Molecules, 2017, vol. 22, pp. 117–136. https://doi.org/10.3390/molecules22010117
Dong, Y., Chollet, J., Matile, H., et al., J. Med. Chem., 2005, vol. 48, pp. 4953–4961. https://doi.org/10.1021/jm049040u
O'Neil, P.M., Expert Opin. Investig. Drugs, 2005, vol. 14, pp. 1117–1128. https://doi.org/10.1517/13543784.14.9.1117
Tang, Y., Dong, Y., Wittlin, S., et al., Bioorg. Med. Chem. Lett., 2007, vol. 17, pp. 1260–1265. https://doi.org/10.1016/j.bmcl.2006.12.007
Dong, Y., Wittlin, S., Sriraghavan, K., et al., J. Med. Chem., 2010, vol. 53, no. 1, pp. 481–491. https://doi.org/10.1021/jm901473s
Padmanilayam, M., Scorneaux, B., Dong, Y., et al., Bioorg. Med. Chem. Lett., 2006, vol. 16, pp. 5542–5545. https://doi.org/10.1016/j.bmcl.2006.08.046
Pearson, R.G., J. Am. Chem. Soc., vol. 85, pp. 3533–3539. https://doi.org/10.1021/ja00905a001
Denekamp, C., Gottlieb, L., Tamiri, T., et al., Org. Lett., 2005, vol. 7, pp. 2461–2464. https://doi.org/10.1021/ol050801c
ACKNOWLEDGMENTS
The structural studies of the products of synthesis were carried out at the Center for Collective Use “Agidel” of the Institute of Petrochemistry and Catalysis, RAS.
Funding
This work was supported by the Russian Science Foundation (RNF project no. 18-73-00014).
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Translated by Z. Svitanko
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Makhmudiyarova, N.N., Ishmukhametova, I.R., Ibragimov, A.G. et al. Synthesis of a New Class of Macrocyclic Phosphorus-Containing Tri- and Diperoxides in the Presence of Lanthanide Catalysts. Dokl Chem 492, 93–98 (2020). https://doi.org/10.1134/S001250082036001X
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DOI: https://doi.org/10.1134/S001250082036001X