SYNTHESIS OF A POLYFUNCTIONAL DENDRON BASED ON GALLIC ACID USING THE AZIDE-ALKYNE CYCLOADDITION REACTION

А. M. Fatykhova; Фатыхова А. М.; V. A. Burilov; Бурилов В. А.; S. E. Solovieva; Соловьева С. Е.; I. S. Antipin; Антипин И. С.

doi:10.31857/S2686953522600830

SYNTHESIS OF A POLYFUNCTIONAL DENDRON BASED ON GALLIC ACID USING THE AZIDE-ALKYNE CYCLOADDITION REACTION

Authors: Fatykhova А.M.¹, Burilov V.A.¹, Solovieva S.E.², Antipin I.S.¹
Affiliations:
1. Kazan Federal University
2. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of Russian Academy of Sciences
Issue: Vol 513, No 1 (2023)
Pages: 11-17
Section: ХИМИЯ
URL: https://journals.rcsi.science/2686-9535/article/view/252487
DOI: https://doi.org/10.31857/S2686953522600830
EDN: https://elibrary.ru/QSDKPP
ID: 252487

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Abstract
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Abstract

By stepwise modification of gallic acid using an azide-alkyne cycloaddition reaction, a first-generation triazole-containing dendron with hydroxypropyltriazole groups and a tetraethylene glycol linker was obtained for the first time. The structure of all intermediate compounds has been proven by modern physical methods. It has been established that the use of bromomethylene derivatives of gallic acid in the synthesis of triazole-containing dendrons results in the formation of by-products of alkylation of the bases used in the reaction (triethylamine and diisopropylethylamine) due to the high mobility of the bromine atom in the benzyl position.

Keywords

dendrimers, gallic acid, click chemistry

References

Antipin I.S., Alfimov M.V., Arslanov V.V., Burilov V.A., Vatsadze S.Z., Voloshin Y.Z., Volcho K.P., Gorbatchuk V.V., Gorbunova Y.G., Gromov S.P., Dudkin S.V., Zaitsev S.Y., Zakharova L.Y., Ziganshin M.A., Zolotukhina A.V., Kalinina M.A., Karakhanov E.A., Kashapov R.R., Koifman O.I., Konovalov A.I., Korenev V.S., Maksimov A.L., Mamardashvili N.Z., Mamardashvili G.M., Martynov A.G., Mustafina A.R., Nugmanov R.I., Ovsyannikov A.S., Padnya P.L., Potapov A.S., Selektor S.L., Sokolov M.N., Solovieva S.E., Stoikov I.I., Stuzhin P.A., Suslov E.V., Ushakov E.N., Fedin V.P., Fedorenko S.V., Fedorova O.A., Fedorov Y.V., Chvalun S.N., Tsivadze A.Y., Shtykov S.N., Shurpik D.N., Shcherbina M.A., Yakimova L.S. // Russ. Chem. Rev. 2021. V. 90. № 8. P. 895–1101. https://doi.org/10.1070/RCR5011
Arzhakova O.V., Arzhakov M.S., Badamshina E.R., Bryuzgina E.B., Bryuzgin E.V., Bystrova A.V., Vaga-nov G.V., Vasilevskaya V.V., Vdovichenko A.Yu., Gallya-mov M.O., Gumerov R.A., Didenko A.L., Zefirov V.V., Karpov S.V., Komarov P.V., Kulichikhin V.G., Kuroch-kin S.A., Larin S.V., Malkin A.Ya., Milenin S.A., Muzafarov A.M., Molchanov V.S., Navrotskiy A.V., Novakov I.A., Panarin E.F., Panova I.G., Potemkin I.I., Svetlichny V.M., Sedush N.G., Serenko O.A., Uspenskii S.A., Philippova O.E., Khokhlov A.R., Chvalun S.N., Sheiko S.S., Shibaev A.V., Elmanovich I.V., Yudin V.E., Yakimansky A.V., Yaroslavov A.A. // Russ. Chem. Rev. 2022. V. 91. P. 12. https://doi.org/10.57634/RCR5062
Yamamoto K., Imaoka T., Tanabe M., Kambe T. // Chem. Rev. 2019. V. 120. № 2. P. 1397–1437. https://doi.org/10.1021/acs.chemrev.9b00188
Newkome G.R., Yao Z.Q., Baker G.R., Gupta V.K. // J. Org. Chem. 1985. V. 50. № 11. P. 2003–2004. https://doi.org/10.1021/jo00211a052
Miller T.M., Neenan T.X. // Chem. Mater. 1990. V. 2. № 4. P. 346–349. https://doi.org/10.1021/cm00010a006
Kolb H.C., Finn M.G., Sharpless K.B. // Angew. Chem., Int. Ed. 2001. V. 40. № 11. P. 2004–2021. https://doi.org/10.1002/1521-3773(20010601)40:11< 2004::AID-ANIE2004>3.0.CO;2-5
Meldal M., Tornøe C.W. // Chem. Rev. 2008. V. 108. № 8. P. 2952–3015. https://doi.org/10.1021/cr0783479
Parshad B., Yadav P., Kerkhoff Y., Mittal A., Achazi K., Haag R., Sharma S.K. // New J. Chem. 2019. V. 43. № 30. P. 11984–11993. https://doi.org/10.1039/C9NJ02612F
Wu P., Feldman A.K., Nugent A.K., Hawker C.J., Scheel A., Voit B., Pyun J., Fréchet J.M.J., Sharpless K.B., Fokin V.V. // Angew. Chem. 2004. V. 116. № 30. P. 4018–4022. https://doi.org/10.1002/ange.200454078
Arseneault M., Levesque I., Morin J.F. // Macromolecules. 2012. V. 45. № 9. P. 3687–3694. https://doi.org/10.1021/ma300648r
Agrahari A.K., Singh A.S., Mukherjee R., Tiwari V.K. // RSC Adv. 2020. V. 10. № 52. P. 31553–31562. https://doi.org/10.1039/D0RA05289B
Qin T., Li X., Chen J., Zeng Y., Yu T., Yang G., Li Y. // Chem. Asian J. 2014. V. 9. № 12. P. 3641–3649. https://doi.org/10.1002/asia.201402960
Mu S., Liu W., Ling Q., Liu X., Gu H. // Appl. Organomet. Chem. 2019. V. 33. № 6. P. e4908. https://doi.org/10.1002/aoc.4908
Camponovo J., Ruiz J., Cloutet E., Astruc D. // Chem. Eur. J. 2009. V. 15. № 12. P. 2990–3002. https://doi.org/10.1002/chem.200801999
Liu Y., Liu G.X., Zhang W., Du C., Wesdemiotis C., Cheng S.Z.D. // Macromolecules. 2019. V. 52. № 11. P. 4341–4348. https://doi.org/10.1021/acs.macromol.9b00549
Palmans A.R.A., Vekemans J.A.J.M., Fischer H., Hik-met R.A., Meijer E.W. // Chem. Eur. J. 1997. V. 3. № 2. P. 300–307. https://doi.org/10.1002/chem.19970030220
Armarego W.L.F. Purification of laboratory chemicals. 8th ed. Elsevier, Butterworth-Heinemann, 2017.
Wijtmans M., de Graaf C., de Kloe G., Istyastono E.P., Smit J., Lim H., Boonnak R., Nijmeijer S., Smits R.A., Jongejan A., Zuiderveld O., de Esch I.J.P., Leurs R. // J. Med. Chem. 2011. V. 54. № 6. P. 1693–1703. https://doi.org/10.1021/jm1013488
Chen H., Hou S., Tan Y. // Supramol. Chem. 2016. V. 28. № 9–10. P. 801–809. https://doi.org/10.1080/10610278.2016.1142089
Heller P., Mohr N., Birke A., Weber B., Reske-Kunz A., Bros M., Barz M. // Macromol. Biosci. 2015. V. 15. № 1. P. 63–73. https://doi.org/10.1002/mabi.201400417