Abstract
1-Carboxymethyl-5-fluoro-5-halogeno-6-hydroxy-5,6-dihydrouracils and 1-carboxymethyl- 5-fluoro-6-hydroxy-5-nitro-5,6-dihydrouracil were synthesized in high yields by oxidative halogenation or nitration of 1-carboxymethyl-5-fluorouracil. Oxidative halogenation or nitration of 5-fluoro-1-(methoxycarbonylmethyl)uracil in acidic media results in the addition of the corresponding groups at the C(5) atom of uracil and simultaneous hydrolysis of the ester group. Bimolecular ions of the obtained compounds were detected in the negative ion mass spectra.
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References
R. Duschinsky, E. Pleven, C. Heidelberger. J. Am. Chem. Soc., 1957, 79, 4559.
C. Heidelberger, N. K. Chaudhuri, P. Danneberg, D. Mooren, L. Griesbach, R. Duschinsky, R. J. Schnitzer, E. Pleven, J. Scheiner. Nature, 1957, 179, 663.
F. J. Ansfield, A. R. Curreri. J. Nat. Cancer Inst., 1959, 22, 497.
R. D. Safaev, V. I. Babskyi, V. A. Suriko, V. S. Khilko, 2007, http://www.oncology.ru/specialist/journal_oncology/archive/0408/015.pdf.
D. V. Mal´tseva, G. S. Zakharova, S. A. Rodin, A. G. Tonevitsky. Russ. Chem. Bull., 2018, 57, 2148.
Yu. I. Murinov, S. A. Grabovskii, N. N. Kabal´nova. Russ. Chem. Bull., 2019, 68, 946.
A. R. Gimadieva, Yu. N. Tchernyshenko, A. G. Mustaphin, I. B. Abdrachmanov. Bash. Khim. Zhurn. [Bashkir J. of Chem.], 2007, 14, No. 3, 5 (in Russian).
A. G. Mustaphin, A. R. Gimadieva, A. K. Fattakhov, I. B. Abdrachmanov. Vestn. Bash. Unta [Bull. Bashkir Univ.], 2010, 15, No. 3, 575 (in Russian).
A. G. Mustaphin, A. R. Gimadieva, I. B. Abdrachmanov, G. A. Tolstikov. Khimiya v Interesah Ustoich. Razvitiya [Chemistry for Sustainable Development], 2008, 16, No. 6, 735 (in Russian).
A. R. Gimadieva. Syntez, modificatsii i biologitcheskaya activnost uracilov [Synthesis, Modifications and Biological Activity of Uracils], Izdvo Gilem, Ufa, 2013, 176 pp. (in Russian).
I. B. Chernikova, S. L. Khursan, M. Yu. Eropkin, M. S. Yunusov. Pharm. Chem. J. (Engl. Transl.), 2019, 53, 108.
D.-Z. Li, Q.-Z. Zhang, C.-Y. Wang, Y.-L. Zhang, X.-Y. Li, J.-T. Huang, H.-Y. Liu, Zh.-D. Fu, H.-X. Song, J.-P. Lin, T.-F. Ji, X.-D. Pan. Eur. J. Med. Chem, 2017, 125, 1235.
X.-H. Xu, G.-M. Yao, Y.-M. Li, J.-H. Lu, Ch.-J. Lin, X. Wang, Ch.-H. Kong. J. Nat. Prod, 2003, 66, 285.
I. B. Chernikova, S. L. Khursan, L. V. Spirikhin, M. S. Yunusov. Chem. Heterocycl. Compd, 2015, 51, 568.
V. G. Kasradze, I. B. Ignat’eva, R. A. Khusnutdinov, K. Yu. Suponitsky, M. Yu. Antipin, M. S. Yunusov. Chem. Heterocycl. Compd., 2012, 48, 1018.
I. B. Chernikova, I. Z. Sagadatova, M. S. Yunusov, R. F. Talipov. Russ. J. Org. Chem., 2019, 55, 325.
A. J. Kirby. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, Berlin, 1983, 149 pp.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0114–0117, January, 2020.
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Chernikova, I.B., Yunusov, M.S. & Mustaphin, A.G. Electrophilic addition to the multiple bond of 1-carboxymethyl-5-fluorouracil. Russ Chem Bull 69, 114–117 (2020). https://doi.org/10.1007/s11172-020-2731-9
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DOI: https://doi.org/10.1007/s11172-020-2731-9