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Adamantylation of Adenine and Related Compounds with Adamantanols in Trifluoroacetic Acid

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Abstract

The adamantylation of adenine and N6-methyl- and N6,N6-dimethyladenines with 3-R-adamantan-1-ols (R = H, iso-Pr, CH2COOH, uracil-5-yl) in trifluoroacetic acid gave of 9-(3-R-adamantan-1-yl)adenines. The structures of 9-(adamantan-1-yl)- and N6-methyl-9-(adamantan-1-yl)adenines were proved by XRD analysis.

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REFERENCES

  1. Nasrallah, H. and Hierso, J.-C., Chem. Mater., 2019, vol. 31, p. 619. https://doi.org/10.1021/acs.chemmater.8b04508

    Article  CAS  Google Scholar 

  2. Wanka, L., Iqbal, K., and Schreiner, P.R., Chem. Rev., 2013, vol. 113, p. 3516. https://doi.org/10.1021/cr100264t

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Agnew-Francis, K.A. and Williams, C.M., Adv. Synth. Catal., 2016, vol. 358, p. 675. https://doi.org/10.1002/adsc.201500949

    Article  CAS  Google Scholar 

  4. Shokova, E.A. and Kovalev, V.V., Pharm. Chem. J., 2013, vol. 47, p. 264. https://doi.org/10.1007/s11094-013-0942-1

    Article  CAS  Google Scholar 

  5. Shokova, E.A. and Kovalev, V.V., Pharm. Chem. J., 2016, vol. 50, p. 63. https://doi.org/10.1007/s11094-016-1400-7

    Article  CAS  Google Scholar 

  6. Rosemeyer, H., Chem. Biodiv., 2004, vol. 1, p. 361. https://doi.org/10.1002/cbdv.200490033

    Article  CAS  Google Scholar 

  7. Aigami, K., Inamoto, Y., Takaishi, N., Hattori, K., Takatsuki, A., and Tamura, G., J. Med. Chem., 1975, vol. 18, p. 713. https://doi.org/10.1021/jm00241a015

    Article  CAS  PubMed  Google Scholar 

  8. Kazimierczuk, Z. and Orzeszko, A., Helv. Chim. Acta, 1999, vol. 82, p. 2020. https://doi.org/10.1002/(sici)1522-2675(19991110)82:

    Article  CAS  Google Scholar 

  9. Maurin, J.K., Lasek, W., Gorska, A., Switaj, T., Jakubowska, A.B., and Kazimierczuk, Z., Chem. Biodiv., 2004, vol. 1, p. 1498. https://doi.org/10.1002/cbdv.200490110

    Article  CAS  Google Scholar 

  10. Rouchal, M., Necas, M., and Vicha, R., Acta Crystallogr., Sect. E, 2009, vol. 65, p. o1268. https://doi.org/10.1107/S1600536809016596

  11. Kavai, I., Mead, L.H., Drobniak, J., and Zakrzewski, S.F., J. Med. Chem., 1975, vol. 18, p. 272. https://doi.org/10.1021/jm00237a012

    Article  CAS  PubMed  Google Scholar 

  12. Young, R.C., Jones, M., Milliner, K.J., Rana, K.K., and Ward, J.G., J. Med. Chem., 1990, vol. 33, p. 2073. https://doi.org/10.1021/jm00170a00

    Article  CAS  PubMed  Google Scholar 

  13. Dejmek, M., Kovačková, S., Zborníková, E., Hřebabecký, H., Šála, M., Dračínský, M., and Nencka, R., RSC Adv., 2012, vol. 2, p. 6970. https://doi.org/10.1039/c2ra20842c

    Article  CAS  Google Scholar 

  14. Shmailov, A., Alimbarova, L., Shokova, E., Tafeenko, V., Vatsouro, I., and Kovalev, V., Tetrahedron, 2010, vol. 66, p. 3058. https://doi.org/10.1016/j.tet.2010.02.043

    Article  CAS  Google Scholar 

  15. Shokova, E., Mousoulou, T., Lyzikov, Yi., and Kovalev, V., Synthesis, 1997, p. 1034. https://doi.org/10.1055/s-1997-1304

  16. Joule, J.A. and Mills, K., Heterocyclic Chemistry, 5th Edn., Manchester: Wiley, 2010, p. 516.

  17. CCDC 2032369 (3b·CF3COOH) and CCDC 2032371 (5) contain crystallographic data for this article. This data is available at: www.ccdc.cam.ac.uk/data_request/cif.

  18. Kovalev, V., Shokova, E., and Rozov, A., Tetrahedron, 1996, vol. 52, p. 3983. https://doi.org/10.1016/S0040-4020(96)00062-2

    Article  CAS  Google Scholar 

  19. Kim, J.K., Shokova, E., Tafeenko, V., and Kovalev, V., Beilstein J. Org. Chem., 2014, p. 2270. https://doi.org/10.1039/D0OB01228A

  20. Kumar, M., Berkson, Z.J., Clark, R.J., Shen, Y., Prisco, N.A., Zheng, Q., Zeng, Z., Zheng, H., McCusker, L.B., Palmer, J.C., Chmelka, B.F., and Rimer, J.D., J. Am. Chem. Soc., 2019, vol. 141, p. 20155. https://doi.org/10.1021/jacs.9b09697

    Article  CAS  PubMed  Google Scholar 

  21. Bott, K., Chem. Ber., 1968, vol. 101, p. 564. https://doi.org/10.1002/cber.19681010225

    Article  CAS  Google Scholar 

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Funding

The work was performed in the framework of the State order “Petrochemistry and Catalysis. Rational Use of Hydrocarbon Raw Materials” (project no. 121031300092-6).

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Authors and Affiliations

  1. Lomonosov Moscow State University, 119991, Moscow, Russia

    V. V. Kovalev, E. A. Shokova & V. A. Tafeenko

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  1. V. V. Kovalev
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  2. E. A. Shokova
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  3. V. A. Tafeenko
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Correspondence to V. V. Kovalev.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 8, pp. 1177–1184 https://doi.org/10.31857/S0514749221080097.

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Kovalev, V.V., Shokova, E.A. & Tafeenko, V.A. Adamantylation of Adenine and Related Compounds with Adamantanols in Trifluoroacetic Acid. Russ J Org Chem 57, 1295–1301 (2021). https://doi.org/10.1134/S1070428021080091

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