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Cyclocondensation of Methyl 5-Methyl-1-(2-oxo-2-phenylethyl)-1H-pyrazole-3-carboxylate. Synthesis of a New 18-Membered Nitrogen Macroheterocycle

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Abstract

A method has been developed for the synthesis of a new 18-membered nitrogen macroheterocycle via acid-catalyzed cyclocondensation of 1-[(2E,Z)-2-hydrazinylidene-2-phenylethyl]-5-methyl-1H-pyrazole-3-carbohydrazide which was obtained by hydrazinolysis of methyl 5-methyl-1-(2-oxo-2-phenylethyl)-1H-pyra­zole-3-carboxylate.

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REFERENCES

  1. Vinogradov, A.A., Yin, Y., and Suga, H., J. Am. Chem. Soc., 2019, vol. 141, p. 4167. https://doi.org/10.1021/jacs.8b13178

    Article  CAS  PubMed  Google Scholar 

  2. Peacock, H. and Suga, H., Trends Pharmacol. Sci., 2021, vol. 42, no. 5, p. 385. https://doi.org/10.1016/j.tips.2021.02.004

    Article  CAS  PubMed  Google Scholar 

  3. Ushakov, E.N., Alfimov, M.V., and Gromov, S.P., Macroheterocycles, 2010, vol. 3, no. 4, p. 189. https://doi.org/10.6060/mhc2010.4.189

    Article  CAS  Google Scholar 

  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., and Mojzych, M., Appl. Sci., 2022, vol. 12, article no. 1102. https://doi.org/10.3390/app12031102

  5. Marsault, E. and Peterson, M.L., J. Med. Chem., 2011, vol. 54, p. 1961. https://doi.org/10.1021/jm1012374

    Article  CAS  PubMed  Google Scholar 

  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., and Nolt, R.J.M., Nat. Commun., 2020, vol. 11, article no. 5291. https://doi.org/10.1038/s41467-020-19123-y

  7. Beletskaya, I.P., Averin, A.D., Pleshkova, N.A., Borisenko, A.A., Serebryakova, M.V., Denat, F., and Guilard, R., Synlett, 2005, vol. 2005, no. 1, p. 87. https://doi.org/10.1055/s-2004-836040

    Article  CAS  Google Scholar 

  8. Ishmuratov, G.Yu., Yakovleva, M.P., Mingaleeva, G.R., and Tolstikov, A.G., Macroheterocycles, 2011, vol. 4, no. 4, p. 270. https://doi.org/10.6060/mhc2011.4.06

    Article  CAS  Google Scholar 

  9. Lawson, A.D.G., MacCoss, M., and Heer, J.P., J. Med. Chem., 2018, vol. 61, no. 10, p. 4283. https://doi.org/10.1021/acs.jmedchem.7b01120

    Article  CAS  PubMed  Google Scholar 

  10. Kharaneko, A.O. and Kharaneko, O.I., Russ. J. Org. Chem., 2018, vol. 54, p. 742. https://doi.org/10.1134/S1070428018050111

    Article  CAS  Google Scholar 

  11. Kharaneko, A.O., Pekhtereva, T.M., and Kharane­ko, O.I., Russ. J. Org. Chem., 2020, vol. 56, p. 95. https://doi.org/10.1134/S1070428020010169

    Article  CAS  Google Scholar 

  12. Kharaneko, A.O., Russ. J. Org. Chem., 2017, vol. 53, p. 738. https://doi.org/10.1134/S1070428017050153

    Article  CAS  Google Scholar 

  13. Kharaneko, A.O., Pekhtereva, T.M., and Kharane­ko, O.I., Russ. J. Org. Chem., 2020, vol. 56, p. 654. https://doi.org/10.1134/S1070428020040144

    Article  CAS  Google Scholar 

  14. Kharaneko, A.O., Pekhtereva, T.M., and Kharane­ko, O.I., Russ. J. Org. Chem., 2020, vol. 56, p. 95. https://doi.org/10.1134/S1070428020010169

    Article  CAS  Google Scholar 

  15. Kharaneko, A.O. and Kharaneko, O.I., Russ. J. Org. Chem., 2019, vol. 55, p. 291. https://doi.org/10.1134/S1070428019030023

    Article  CAS  Google Scholar 

  16. Shutaleva, A.D., Fesenko, A.A., Yankov, A.N., Tafeen­ko, V.A., and Chernyshev, V.V., J. Mol. Struct., 2017, vol. 1150, p. 349. https://doi.org/10.1016/j.molstruc.2017.08.096

    Article  CAS  Google Scholar 

  17. Ramakrishnan, A., Chourasiya, S.S., and Bharatam, P.V., RSC Adv., 2015, vol. 5, no. 69, p. 55938. https://doi.org/10.1039/c5ra05574a

    Article  CAS  Google Scholar 

  18. Sharma, A., Jad, Y., Siddiqui, M.R.H., Torre, B.G., Albericio, F., and El-Faham, A., J. Chem., 2017, article ID 5702962. https://doi.org/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., and Montgomery, J.A., Jr., J. Comput. Chem., 1993, vol. 14, no. 11, p. 1347. https://doi.org/10.1002/jcc.540141112

    Article  CAS  Google Scholar 

  21. CrysAlisPro, version 1.171.38.41, Rigaku Oxford Diffraction, Oxford, 2015.

  22. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053273314026370

    Article  CAS  Google Scholar 

  23. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  24. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crys­tallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

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Funding

This study, in particular development of the synthetic strategy and its implementation, physicochemical studies, and interpretation of the results, was performed at the Litvinenko Institute of Physical Organic and Coal Chemistry with financial support from the Ministry of Science and Higher Education of the Russian Federation (project no. FRES-2023-0004). A part of the study including quantum chemical calculations of the structure and tautomerism of the macrocyclic product and interpretation of the calculation results was carried out at the Southern Federal University with financial support from the Ministry of Science and Higher Education of the Russian Federation (project no. FENW-2023-0011).

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, 283048, Donetsk, Russia

    A. O. Kharaneko, T. M. Pekhtereva & O. I. Kharaneko

  2. Research Institute of Physical and Organic Chemistry, Southern Federal University, 344090, Rostov-on-Don, Russia

    A. O. Kharaneko & A. S. Morkovnik

Authors
  1. A. O. Kharaneko
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  2. T. M. Pekhtereva
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  3. O. I. Kharaneko
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  4. A. S. Morkovnik
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Correspondence to A. O. Kharaneko.

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Kharaneko, A.O., Pekhtereva, T.M., Kharaneko, O.I. et al. Cyclocondensation of Methyl 5-Methyl-1-(2-oxo-2-phenylethyl)-1H-pyrazole-3-carboxylate. Synthesis of a New 18-Membered Nitrogen Macroheterocycle. Russ J Org Chem 60, 430–436 (2024). https://doi.org/10.1134/S1070428024030096

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