Email this article Modification of N-functionalized 4-nitroso-1H-pyrazoles
- Authors: 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
-
Affiliations:
- 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
- Issue: Vol 60, No 5 (2024)
- Pages: 654-659
- Section: Articles
- URL: https://journal-vniispk.ru/0514-7492/article/view/279750
- DOI: https://doi.org/10.31857/S0514749224050091
- EDN: https://elibrary.ru/RCVSVA
- ID: 279750
Cite item
Open Access
Access granted
Abstract
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.
Keywords
Full Text
About the authors
A. V. Bobrova
Reshetnev Siberian State University of Science and Technology
Author for correspondence.
Email: anastasiya-an-96@mail.ru
ORCID iD: 0000-0002-9264-4449
Russian Federation, Krasnoyarskii Rabochii prosp., 31, Krasnoyarsk, 660037
E. I. Golenko
Reshetnev Siberian State University of Science and Technology
Email: anastasiya-an-96@mail.ru
ORCID iD: 0009-0001-1413-6318
Russian Federation, Krasnoyarskii Rabochii prosp., 31, Krasnoyarsk, 660037
A. V. Oberenko
Siberian Federal University
Email: anastasiya-an-96@mail.ru
ORCID iD: 0000-0002-1156-9644
Russian Federation, Svobodny prosp., 79, Krasnoyarsk, 660041
T. Y. 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
Russian Federation, Akademgorodok, 50/24, Krasnoyarsk, 660036
E. V. 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
Russian Federation, Krasnoyarskii Rabochii prosp., 31, Krasnoyarsk, 660037; ul. Partizana Zheleznyaka, 1, Krasnoyarsk, 660022
G. A. Suboch
Reshetnev Siberian State University of Science and Technology
Email: anastasiya-an-96@mail.ru
ORCID iD: 0000-0003-2027-8512
Russian Federation, Krasnoyarskii Rabochii prosp., 31, Krasnoyarsk, 660037
References
- 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
Supplementary files
