Mechanochemical fluorination of naproxen and its salts with F-TEDA-BF4
- Авторлар: Borodkin G.I.1, Elanov I.R.1, Shubin V.G.1
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Мекемелер:
- Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences
- Шығарылым: Том 59, № 11 (2023)
- Беттер: 1418-1426
- Бөлім: Articles
- URL: https://kazanmedjournal.ru/0514-7492/article/view/667133
- DOI: https://doi.org/10.31857/S0514749223110034
- EDN: https://elibrary.ru/NHKYSI
- ID: 667133
Дәйексөз келтіру
Аннотация
The mechanochemical fluorination of naproxen and its salts (Li, Na and K) using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™, F-TEDA-BF4) has been studied. The reaction of naproxen with an excess of Selectfluor gives 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalene-2-yl)propionic acid in high yield. The use of a small amount of Al2O3, SiO2, M2CO3 (M = Na, K, Rb, Cs), ionic liquids (ILs), crown ethers, and N-bases enhances the rate of reaction of naproxen with Selectfluor and increases the proportion of the monofluorination product compared to the difluorination product.
Негізгі сөздер
Авторлар туралы
G. Borodkin
Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences
Email: gibor@nioch.nsc.ru
I. Elanov
Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences
V. Shubin
Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences
Әдебиет тізімі
- Ilyas S., Jilani K., Sikandar M., Siddiq S., Riaz M., Naveed A., Bibi I., Nawaz H., Irfan M., Asghar A. Dose Response Inter. J. 2020, 18, 1-6. doi: 10.1177/1559325819899259
- Saji R.S., Prasana J.C., Muthu S., George J., Kuruvilla T.K., Raajaraman B.R. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2020, 226, 117614. doi: 10.1016/j.saa.2019.117614
- Mohammed A., Yarla N.S., Madka V., Rao C.V. Int. J. Mol. Sci. 2018, 19, 2332-2349. doi: 10.3390/ijms19082332
- Hui D.S., Lee N., Chan P.K., Beigel J.H. Antivir. Res. 2018, 150, 202-216. doi: 10.1016/j.antiviral.2018.01.002
- Lejal N., Tarus B., Bouguyon E., Chenavas S., Bertho N., Delmas B., Ruigrok R.W.H., Primo C.D., Slama-Schwok A. Antimicrob. Agents Chemother. 2013, 57, 2231-2242. doi: 10.1128/AAC.02335-12
- Yerien D.E., Bonesi S, Postigo A. Org. Biomol. Chem. 2016, 14, 8398-8427. doi: 10.1039/c6ob00764c
- Zaikin P.A., Borodkin G.I. Late-Stage Fluorination of Bioactive Molecules and Biologically-Relevant Substrates. Ed. A. Postigo. Amsterdam: Elsevier. 2019, 105-135.
- Gillis E.P., Eastman K.J., Hill M.D., Donnelly D.J., Meanwell N.A. J. Med. Chem. 2015, 58, 8315-8359. doi: 10.1021/acs.jmedchem.5b00258
- Alvarez F.S. Пат. 3637767A (1972). США
- Schlosser M., Michel D., Guo Z.-w., Sih C.J. Tetrahedron. 1996, 52, 8257-8262. doi: 10.1016/0040-4020(96)00411-5
- Goj O., Kotila S., Haufe G. Tetrahedron. 1996, 52, 12761-12774. doi: 10.1016/0040-4020(96)00758-2
- Fujisawa H.,Fujiwara T., Takeuchi Y., Omata K. Chem. Pharm. Bull. 2005, 53, 524-528. doi: 10.1248/cpb.53.524
- Borodkin G.I., Elanov I.R., Gatilov Yu.V., Shubin V.G. J. Fluor. Chem. 2019, 228, 109412. doi: 10.1016/j.jfluchem.2019.109412
- Tan D., Friščić T. Eur. J. Org. Chem. 2018, 18-33. doi: 10.1002/ejoc.201700961
- Бородкин Г.И., Шубин В.Г. ЖОрХ. 2021, 57, 1209-1242.
- Borodkin G.I., Shubin V.G. Russ. J. Org. Chem. 2021, 57, 1369-1397. doi: 10.1134/S1070428021090013
- Zaikin P.A., Dyan Ok Ton, Elanov I.R., Borodkin G.I. Molecules. 2021, 26, 5756. doi: 10.3390/molecules26195756
- Gomollón-Bel F. Chem. Int. 2019, 41, 12-17. doi: 10.1515/ci-2019-0203
- Ionic Liquids in Synthesis. Eds. P. Wasserscheid, T. Welton. Weinheim: Wiley, 2008. doi: 10.1002/9783527621194
- Sandhu S., Sandhu J.S. Green Chem. Lett. Rev. 2011, 4, 289-310. doi: 10.1080/17518253.2011.572294
- Maton C., Vos N.D., Stevens C.V. Chem. Soc. Rev. 2013, 42, 5963-5977. doi: 10.1039/c3cs60071h
- Бородкин Г.И., Шубин В.Г. ЖОрХ. 2006, 42, 1761-1783.
- Borodkin G.I., Shubin V.G. Russ. J. Org. Chem. 2006, 42, 1745-1770. doi: 10.1134/S1070428006120013
- Laali K.K., Borodkin G.I. J. Chem. Soc., Perkin Trans. 2. 2002, 953-957. doi: 10.1039/b111725d
- Heravi M.R.P. J. Fluor. Chem. 2008, 129, 217-221. doi: 10.1016/j.jfluchem.2007.11.006
- Pavlinac J., Zupan M., Laali K.K., Stavber S. Tetrahedron. 2009, 65, 5625-5662. doi: 10.1016/j.tet.2009.04.092
- Bogautdinov R.P., Fidarov A.F., Morozkina S.N., Zolotarev A.A., Starova G.L., Selivanov S.I., Shavva A.G. J. Fluor. Chem. 2014, 168, 218-222. doi: 10.1016/j.jfluchem.2014.09.030
- Laali K.K. Arkivoc. 2016, i, 50-171. doi: 10.3998/ark.5550190.p009.490
- Gu Q., Vessally E. RSC Adv. 2020, 10, 6756-16768. doi: 10.1039/D0RA00324G
- Timofeeva D.S., Ofial A.R., Mayr H. J. Am. Chem. Soc. 2018, 140, 11474-11486. doi: 10.1021/jacs.8b07147
- Zaikin P.A., Dyan Ok Ton, Evtushok D.V., Usoltsev A.N., Borodkin G.I., Karpova E.V., Shubin V.G. Eur. J. Org. Chem. 2017, 2469-2474. doi: 10.1002/ejoc.201700179
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