- PII
- S30346304S0514749225050047-1
- DOI
- 10.7868/S3034630425050047
- Publication type
- Article
- Status
- Published
- Authors
- Volume/ Edition
- Volume 61 / Issue number 5
- Pages
- 544-551
- Abstract
- A method for the synthesis of a new 18-membered nitrogen macroheterocycle was developed. It was based on the acid-catalytic cyclocondensation of 1-[(2E,Z)-2-hydrazono-2-phenylethyl]-5-methyl-1H-pyrazole-3-carbohydrazide, a reaction product of methyl 5-methyl-1-(2-oxo-2-phenylethyl)-1H-pyrazole-3-carboxylate with hydrazine.
- Keywords
- азотсодержащие макроциклы пиразол-3-карбоксилат гидразин 2-гидразоно-1H-пиразол-3-карбогидразид пиразол-1,2,5-триазепин кислотно-каталитическая циклизация
- Date of publication
- 13.12.2025
- Year of publication
- 2025
- Number of purchasers
- 0
- Views
- 33
References
- 1. Vinogradov A.A., Yin Y., Suga H., J. Am. Chem. Soc. 2019, 141, 4167–4181. doi 10.1021/jacs.8b13178
- 2. Peacock H., Suga H. Trends Pharmacol. Sci. 2021, 42 (5), 385–397. doi 10.1016/j.tips.2021.02.004
- 3. Ushakov E.N., Alfimov M.V., Gromov S.P., Macroheterocycles. 2010, 3 (4), 189–200. doi 10.6060/mhc2010.4.189
- 4. Ullah F., Khan T.A., Iltaf J., Anwar S., Khan M.F.A., Khan M.R., Ullah S., Fayyaz ur Rehman M., Mustaqeem M., Kotwica-Mojzych K., Mojzych M., Appl. Sci. 2022, 12, 1102. doi 10.3390/app12031102
- 5. Marsault E., Peterson M. L., J. Med. Chem. 2011, 54, 1961–2004. doi 10.1021/jm1012374
- 6. Gilissen P.J., White P.B., Berrocal J.A., Vanthuyne N., Rutjes F.P.J.T., Feringa B.L., Elemans J.A.A.W., Nolt R.J.M. Nat. Commun. 2020, 11, 5291–5301. doi 10.1038/s41467-020-19123-y
- 7. Beletskaya I.P., Averin A.D., Pleshkova N.A., Borisenko A.A., Serebryakova M.V., Denat F., Guilard R. Synlett. 2005, 1, 87–90. doi 10.1055/s-2004-836040
- 8. Ишмуратов Г.Ю., Яковлева М.П., Мингалеева Г.Р., Толстиков А.Г. Макрогетероциклы. 2011, 4 (4), 270–310. @@Ishmuratov G.Yu., Yakovleva M.P., Mingaleeva G.R., Tolstikov A.G. Macroheterocycles. 2011, 4 (4), 270–310. doi 10.6060/mhc2011.4.06
- 9. Lawson A.D.G., MacCoss M., Heer J.P. J. Med. Chem. 2018, 61 (10), 4283–4289. doi 10.1021/acs.jmedchem.7b01120
- 10. Харанеко А.О., Харанеко О.И. ЖОрХ. 2018, 54, 738–742. @@Kharaneko A.O. Kharaneko O.I. Russ. J. Org. Chem. 2018, 54, 742–746. doi 10.1134/S1070428018050111
- 11. Харанеко А.О., Пехтерева Т.М., Харанеко О.И. ЖОрХ. 2020, 56, 118–128. @@Kharaneko A.O., Pekhtereva T.M., Kharaneko O.I. Russ. J. Org. Chem. 2020, 56, 95–104. doi 10.1134/S1070428020010169
- 12. Харанеко А.О. ЖОрХ. 2017, 53, 727–734. @@Kharaneko A.O. Russ. J. Org. Chem. 2017, 53, 738–745. doi 10.1134/S1070428017050153
- 13. Харанеко А.О., Пехтерева Т.М., Харанеко О.И. ЖОрХ. 2020, 56, 619–627. @@Kharaneko A.O., Pekhtereva T.M., Kharaneko O.I. Russ. J. Org. Chem. 2020, 56, 654–661. doi 10.1134/S1070428020040144
- 14. Харанеко А.О., Пехтерева Т.М., Харанеко О.И. ЖОрХ. 2020, 56, 118–128. @@Kharaneko A.O., Pekhtereva T.M., Kharaneko O.I. Russ. J. Org. Chem. 2020, 56, 95–104. doi 10.1134/S1070428020010169
- 15. Харанеко А.О., Харанеко О.И. ЖОрХ. 2019, 55, 341–346. @@Kharaneko A.O., Kharaneko O.I. Russ. J. Org. Chem. 2019, 55, 291–295. doi 10.1134/S1070428019030023
- 16. Shutaleva A.D., Fesenko A.A., Yankov A.N., Tafeenko V.A., Chernyshev V.V. J. Mol. Struct. 2017, 1150, 349–357. doi 10.1016/j.molstruc.2017.08.096
- 17. Ramakrishnan A., Chourasiya S.S., Bharatam P.V. RSC Adv. 2015, 5 (69), 55938–5947. doi 10.1039/c5ra05574a
- 18. Sharma A., Jad Y., Siddiqui M.R.H., Torre B.G., Albericio F., El-Faham A. J. Chem., 2017, Article ID 5702962. doi 10.1155/2017/5702962
- 19. Granovsky A.A., Firefly, version 8, http://classic.chem.msu.su/gran/firefly/index.html
- 20. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., Montgomery J.A. J. Comput. Chem. 1993, 14 (11), 1347–1363. doi 10.1002/jcc.540141112
- 21. CrysAlisPro, version 1.171.38.41, Rigaku Oxford Diffraction, Oxford, 2015.
- 22. Sheldrick G.M., Acta Crystallogr., Sect. A: Found. Adv. 2015, 71, 3–8. doi 10.1107/S2053273314026370
- 23. Sheldrick G.M., Acta Crystallogr., Sect. C: Struct. Chem. 2015, 71, 3–8. doi 10.1107/S2053229614024218
- 24. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H.J. Appl. Crystallogr. 2009, 42, 339–341. doi 10.1107/S0021889808042726