Chemical properties of 3-tert-butyl-2-oxo1,2-dihydropyrrolo[1,2-b][1,2,4]triazin-6-carboxylates
- Authors: Ivanov S.M1, Koltun D.S1, Kolotyrkina N.G1
-
Affiliations:
- N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
- Issue: Vol 59, No 4 (2023)
- Pages: 492-506
- Section: Articles
- URL: https://journals.rcsi.science/0514-7492/article/view/144753
- DOI: https://doi.org/10.31857/S0514749223040080
- EDN: https://elibrary.ru/ASIKVD
- ID: 144753
Cite item
Abstract
Alkaline hydrolysis of 6- tert -butyl-8-ethyl-7-amino-3- tert -butyl-2-oxo-1,2-dihydropyrrolo[1,2- b ][1,2,4]triazin6,8-dicarboxylate gave the corresponding 8-carboxylic acid, treatment of which with n -BuBr or NBS/TEA led to the decarboxylation and alkylation of N1, C2O or bromination of the C8 ring position, respectively. Diazotization of 7-amino-3- tert -butyl-8-R1-2-ОR2-pyrrolo[1,2- b ][1,2,4]triazin-6-carboxylates furnished 7-azido (R1 = Br, CO2Et;R1 = H, n -Bu) and 7-unsubstituted (R1 = Br, CN; R2 = n -Bu, CH2CO2Et, CH2Boc) derivatives, and also 7-(1 H -1,2,3-triazol-1-yl)pyrrolo[1,2- b ][1,2,4]triazin-6,8-dicarboxylate. The spectral and X-Ray structural features, as well as antimicrobial activity of the synthesized compounds are considered.
About the authors
S. M Ivanov
N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Email: sergey13iv1@mail.ru
D. S Koltun
N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Email: sergey13iv1@mail.ru
N. G Kolotyrkina
N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Email: sergey13iv1@mail.ru
References
- Debnatha B., Singh W.S., Das M., Goswami S., Singh M.K., Maiti D., Manna K. Mater. Today Chem. 2018, 9, 56-72. doi: 10.1016/j.mtchem.2018.05.001
- Ain Q.-U., Khan H., Mubarak M.S., Pervaiz A. Front Pharmacol. 2016, 7, 292. doi: 10.3389/fphar.2016.00292
- Su C., Yan Y., Guo X., Luo J., Liu C., Zhang Z., Xiang W.-S., Huang S.-X. Org. Biomol. Chem. 2019, 17, 477-481. doi: 10.1039/C8OB02847H
- Ruanpanun P., Laatsch H., Tangchitsomkid N., Lumyong S. World J. Microbiol. Biotechnol. 2011, 27, 1373-1380. doi: 10.1007/s11274-010-0588-z
- Smirnov V.V., Kiprianova E.A., Garagulya A.D., Esipov S.E., Dovjenko S.A. FEMS Microbiol. Lett. 1997, 153, 357-361. doi: 10.1111/j.1574-6968.1997.tb12596.x
- Ivanov S.M. Comprehensive Heterocyclic Chemistry IV. Eds. D.S. Black, J. Cossy, C.V. Stevens, S.J. Gharpure. 2022, 9, 29-180. doi: 10.1016/B978-0-12-818655-8.00062-7
- Ott G.R., Favor D.A. Bioorg. Med. Chem. Lett. 2017, 27, 4238-4246. doi: 10.1016/j.bmcl.2017.07.073
- Воинков Е.К., Дрокин Р.А., Уломский Е.Н., Чупахин О.Н., Чарушин В.Н., Русинов В.Л. ХГС. 2020, 56, 1254-1273.
- Voinkov E.K., Drokin R.A., Ulomsky E.N., Chupakhin O.N., Charushin V.N., Rusinov V.L. Chem. Heterocycl. Compd. 2020, 56, 1254-1273. doi: 10.1007/s10593-020-02808-z
- Voinkov E.K., Drokin R.A., Fedotov V.V., Butorin I.I., Savateev K.V., Lyapustin D.N., Gazizov D.A., Gorbunov E.B., Slepukhin P.A., Gerasimova N.A., Evstigneeva N.P., Zilberberg N.V., Kungurov N.V., Ulomsky E.N., Rusinov V.L. ChemistrySelect. 2022, 7, e202104253. doi: 10.1002/slct.202104253
- Ke Z., Lu T., Liu H., Yuan H., Ran T., Zhang Y., Yao S., Xiong X., Xu J., Xu A., Chen Y. J. Mol. Struct. 2014, 1067, 127-137. doi: 10.1016/j.molstruc.2014.03.036
- Shi W., Qiang H., Huang D., Bi X., Huang W., Qian H. Eur. J. Med. Chem. 2018, 158, 814-831. doi: 10.1016/j.ejmech.2018.09.050
- Paymode D.J., Cardoso F.S.P., Agrawal T., Tomlin J.W., Cook D.W., Burns J.M., Stringham R.W., Sieber J.D., Gupton B.F., Snead D.R. Org. Lett. 2020, 22, 7656-7661. doi: 10.1021/acs.orglett.0c02848
- Astakhina V., Voievudskyi M., Kharchenko O., Novikov V., Komarovska-Porohnyavets E., Petukhova O. J. Heterocycl. Chem. 2016, 53, 421-428. doi: 10.1002/jhet.2204
- Styskala J., Slouka J., Cankar P. Heterocycles. 2008, 75, 1087-1095. doi: 10.3987/COM-07-11267
- Ivanov S.M. Tetrahedron Lett. 2020, 61, 152404. doi: 10.1016/j.tetlet.2020.152404
- Иванов C.М., Тужаров Е.И., Колотыркина Н.Г. ЖОХ. 2021, 91, 1944-1953.
- Ivanov S.M., Tuzharov Е.I., Kolotyrkina N.G. Russ. J. Gen. Chem. 2021, 91, 2453-2461. doi: 10.1134/S1070363221120148
- Миронович Л.М., Костина М.В. ХГС. 2011, 47, 1555-1559.
- Mironovich L.M., Kostina M.V. Chem. Heterocycl. Compd. 2012, 47, 1286-1289. doi: 10.1007/s10593-012-0904-7
- Иванов C.М., Миронович Л.М., Родиновская Л.А., Шестопалов А.М. Изв. АН. Сер. Хим. 2017, 66, 727-731.
- Ivanov S.M., Mironovich L.M., Rodinovskaya L.A., Shestopalov A.M. Russ. Chem. Bull. 2017, 66, 727-731. doi: 10.1007/s11172-017-1801-0
- Parrino B., Spano V., Carbone A., Montalbano A., Barraja P., Matyus P., Cirrincione G., Diana P. Tetrahedron 2014, 70, 7318-7321. doi: 10.1016/j.tet.2014.07.051
- Cirrincione G., Almerico A.M., Aiello E., Dattolo G. Chem. Heterocycl. Compd. Eds. E.C. Taylor, A. Weissberger. 1992, 48, 299-523. doi: 10.1002/9780470187340.ch3
- Ho Z.-C., Livant P., Lott W.B., Webb T.R. J. Org. Chem. 1999, 64, 8226-8235. doi: 10.1021/jo9909608
- Truce W.E., Kruse R.B. J. Am. Chem. Soc. 1959, 81, 5372-5374. doi: 10.1021/ja01529a030
- Методические указания МУК 4.2.1890-04. М.: Федеральный центр госсанэпиднадзора Минздрава России, 2004. 91.
- CLSI, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, 9th ed., CLSI document M07-A9, Clinical and Laboratory Standards Institute, USA, 2012.
- СLSI, Reference Method for Broth Dilution Antifungal Susceptibility Testing Filamentous Fungi, Approved Standard, 2nd ed., CLSI document M38-A2, USA, 2008.
- Bruker. APEX-III. Bruker AXS Inc., Madison, 2018.
- Krause L., Herbst-Irmer R., Sheldrick G.M., Stalke D. J. Appl. Crystallogr. 2015, 48, 3-10. doi: 10.1107/S1600576714022985
- Sheldrick G.M. Acta Crystallogr., Sect. A. 2015, 71, 3-8. doi: 10.1107/S2053273314026370
- Sheldrick G.M. Acta Crystallogr., Sect. C. 2015, 71, 3-8. doi: 10.1107/S2053229614024218