Modification of N-functionalized 4-nitroso-1H-pyrazoles
- Autores: Bobrova A.V.1, Golenko E.I.1, Oberenko A.V.2, Ivanenko T.Y.3, Root E.V.1,4, Suboch G.A.1
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Afiliações:
- Reshetnev Siberian State University of Science and Technology
- Siberian Federal University
- Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center ‘Krasnoyarsk Science Center SB RAS’
- Krasnoyarsk State Medical University named after prof. V.F. Voino-Yasenetsky
- Edição: Volume 60, Nº 5 (2024)
- Páginas: 654-659
- Seção: Articles
- URL: https://ruspoj.com/0514-7492/article/view/685345
- DOI: https://doi.org/10.31857/S0514749224050091
- EDN: https://elibrary.ru/RCVSVA
- ID: 685345
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Resumo
N-substituted 3,5-dimethyl-4-nitroso-1H-pyrazoles was oxidized and reduced. The resulting 4-aminopyrazole was acylated, diazotized with further azo coupling or amino group replacement by iodine. Aminopyrazole was also condensed with 4-nitrobenzaldehyde. The first condensation of nitrosopyrazole with 2,4-dinitrotoluene was shown. As a result, new functionalised pyrazole derivatives were isolated. The structure of novel pyrazoles was confirmed by IR, 1H, 13C NMR spectroscopy, gas chromatography-mass spectrometry, and elemental analysis. The obtained compounds are promising for further research in medicine and pharmaceutical chemistry.
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Sobre autores
A. Bobrova
Reshetnev Siberian State University of Science and Technology
Autor responsável pela correspondência
Email: anastasiya-an-96@mail.ru
ORCID ID: 0000-0002-9264-4449
Rússia, Krasnoyarskii Rabochii prosp., 31, Krasnoyarsk, 660037
E. Golenko
Reshetnev Siberian State University of Science and Technology
Email: anastasiya-an-96@mail.ru
ORCID ID: 0009-0001-1413-6318
Rússia, Krasnoyarskii Rabochii prosp., 31, Krasnoyarsk, 660037
A. Oberenko
Siberian Federal University
Email: anastasiya-an-96@mail.ru
ORCID ID: 0000-0002-1156-9644
Rússia, Svobodny prosp., 79, Krasnoyarsk, 660041
T. Ivanenko
Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center ‘Krasnoyarsk Science Center SB RAS’
Email: anastasiya-an-96@mail.ru
ORCID ID: 0000-0002-1931-3205
Rússia, Akademgorodok, 50/24, Krasnoyarsk, 660036
E. Root
Reshetnev Siberian State University of Science and Technology; Krasnoyarsk State Medical University named after prof. V.F. Voino-Yasenetsky
Email: anastasiya-an-96@mail.ru
ORCID ID: 0009-0001-7093-4701
Rússia, Krasnoyarskii Rabochii prosp., 31, Krasnoyarsk, 660037; ul. Partizana Zheleznyaka, 1, Krasnoyarsk, 660022
G. Suboch
Reshetnev Siberian State University of Science and Technology
Email: anastasiya-an-96@mail.ru
ORCID ID: 0000-0003-2027-8512
Rússia, Krasnoyarskii Rabochii prosp., 31, Krasnoyarsk, 660037
Bibliografia
- Vančik H. Aromatic C-Nitroso Compounds. Dordrecht: Springer Netherlands 2013, 1, 1–156. doi: 10.1007/978-94-007-6337-1
- Huang J., Chen Z., Yuan J., Peng Y. Asian J. Org. Chem. 2016, 5, 951–960. doi: 10.1002/ajoc.201600242
- Astolfi P., Carloni P., Damiani E., Greci L., Marini M., Rizzoli C., Stipa P. Eur. J. Org. Chem. 2008, 19, 3279–3285. doi: 10.1002/ejoc.200800213
- Bobrov P.S., Kirik S.D., Peterson I.V., Suboch G.A. Org. Biomol. Chem. 2023, 21, 3604–3614. doi: 10.1039/D3OB00356F
- Yang W., Lu X., Zhou T., Cao Y., Zhang Y., Ma M. Chem. Heterocycl. Compd. 2018, 54, 780–783. doi: 10.1007/s10593-018-2349-0
- Bobrova A.V., Krasnov P.O., Povarov I.G., Bobrov P.S., Lyubyashkin A.V., Suboch G.A., Tovbis M.S. J. Mol. Struct. 2021, 1230, 129912. doi: 10.1016/j.molstruc.2021.129912
- Maji B., Yamamoto H. J. Am. Chem. Soc. 2015, 137, 15957–15963. doi: 10.1021/jacs.5b11273
- Xu X.-B., Liu Y.-N., Rao G.-W. Russ. J. Org. Chem. 2019, 55, 559–568. doi: 10.1134/s1070428019040237
- Priewisch B., Rück-Braun K. J. Org. Chem. 2005, 70, 2350–2352. doi: 10.1021/jo048544x
- Li W., Xin J., Zhai P., Lin J., Huang S., Gao W., Li X., Org. Biomol. Chem. 2021, 19, 6473–6477. doi: 10.1039/D1OB00930C
- Gulyaev D.A., Klenov M.S., Churakov A.M., Strelenko Y.A., Fedyanin I.V., Lempert D.B., Kosareva E.K., Kon’kova T.S., Matyushin Y.N., Tartakovsky V.A., RSC Adv. 2021, 11, 24013–24021. doi: 10.1039/D1RA03919A
- Bobrova A.V., Krasnov P.O., Radzhabov A.D., Kondrasenko A.A., Root E.V., Suboch G.A. ChemistrySelect 2023, 8, e202302031. doi: 10.1002/slct.202302031
- Боброва А.В., Субоч Г.А., Левченко С.И., Роот Е.В., Пен В.Р. Пат. 2786096 (2022). РФ. Б.И. 2022, № 35.
- Burgart Y.V., Agafonova N.A., Shchegolkov E.V., Krasnykh O.P., Kushch S.O., Evstigneeva N.P., Gerasimova N.A., Maslova V.V., Triandafilova G.A., Solodnikov S.Yu., Ulitko M.V., Makhaeva G.F., Rudakova E.V., Borisevich S.S., Zilberberg N.V., Kungurov N.V., Saloutin V.I., Chupakhin O.N. Eur. J. Org. Chem. 2020, 208, 112768. doi: 10.1016/j.ejmech.2020.112768
- Comes Franchini M., Bonini B.F., Camaggi C.M., Gentili D., Pession A., Rani M., Strocchi E. Eur. J. Org. Chem. 2010, 45, 2024–2033. doi: 10.1016/j.ejmech.2010.01.014
- Abu-Surrah A.S., Abu Safieh K.A., Ahmad I.M., Abdalla M.Y., Ayoub M.T., Qaroush A.K., Abu-Mahtheieh A.M. Eur. J. Org. Chem. 2010, 45, 471–475. doi: 10.1016/j.ejmech.2009.10.029
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