Synthesis of new derivatives of 18-membered macrocycles by cyclocondensation of pyrazole series hydrazine hydrazides

Мұқаба

Дәйексөз келтіру

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Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Рұқсат ақылы немесе тек жазылушылар үшін

Аннотация

Studies on the synthesis of new representatives of 18-membered nitrogenous macrogeterocycles of the biacylhydrazone type based on N-phenacyl- and N-carbalkoxymethylpyrazoles having a carboxyalkyl or acetyl group in the ring carbon atoms were conducted.

Толық мәтін

Рұқсат жабық

Авторлар туралы

A. Kharaneko

Southern Federal University

Хат алмасуға жауапты Автор.
Email: antonhar08@rambler.ru
ORCID iD: 0000-0002-8677-2647

Institute of Physical and Organic Chemistry

Ресей, prosp. Stachki, 194/2, Rostov-on-Don, 344090

A. Morkovnik

Southern Federal University

Email: antonhar08@rambler.ru
ORCID iD: 0000-0002-9182-6101

Institute of Physical and Organic Chemistry

Ресей, prosp. Stachki, 194/2, Rostov-on-Don, 344090

O. Kharaneko

Litvinenko Institute of Physical-Organic and Coal Chemistry

Email: antonhar08@rambler.ru
ORCID iD: 0000-0003-1105-8227
Ресей, ul. R. Luxemburg, 70, Donetsk, 283048

O. Demidov

North-Caucasus Federal University

Email: antonhar08@rambler.ru
ORCID iD: 0000-0002-3586-0487
Ресей, ul. Pushkina, 1a, Stavropol

Әдебиет тізімі

  1. Foldesi T., Dancso A., Simig G., Volk B., Milen M. Tetrahedron. 2016, 72 (35), 5427–5432. doi: 10.1016/j.tet.2016.07.029
  2. Харанеко А.О. ЖОрХ. 2017, 53(5), 727-734. [Kharaneko A.O. Rus. J. Org. Chem. 2017, 53, 738–745.] doi: 10.1134/S1070428017050153
  3. Bohza S., Bohdan N., Stepanova D., Nikolaev A., Suikov S. ChemRxiv. 2022. doi: 10.26434/chemrxiv-2022-p1vj9
  4. Kharaneko A.O., Pekhtereva T.M., Kharaneko O.I., Morkovnik A.S. Russ. J. Org. Chem. 2024, 60, 430–436. doi: 10.1134/S1070428024030096
  5. 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
  6. Chen C., Wei T., Nanoscale Horiz. 2022, 7, 1121–1135. doi: 10.1039/D2NH00242F
  7. Харанеко А.О., Харанеко О.И. ЖОрХ. 2019, 55 (3), 341–346. [Kharaneko A.O., Kharaneko O.I. Russ. J. Org. Chem. 2019, 55(3), 291–295.] doi: 10.1134/S1070428019030023
  8. Харанеко А.О. ЖОрХ. 2016, 52 (6), 904–908. [Kharaneko A.O., Russ. J. Org. Chem. 2016, 52 (6), 892–896.] doi: 10.1134/S1070428016060221
  9. Shutalev A.D., Fesenko A.A., Kuzmina O.M., Volov A.N., Albov D.V., Chernyshev V.V., Zamilatskov I.A. Tetrahedron Lett. 2014, 55, 5481–5485. doi: 10.1016/j.tetlet.2014.08.016
  10. Fesenko A.A., Shutalev A.D. Tetrahedron. 2015, 71, 9528–9543. doi 0.1016/j.tet.2015.10.079
  11. Yamazaki Sh., Lam J.LSh., Johnson T.W. J.L. Practical Medicinal Chemistry with Macrocycles, Ch. 18. Ed. E. Marsault, Wiley, Hoboken, 2017.
  12. Jimenez D.G., Poongavanam V., Kihelbery J. J. Med. Chem. 2023, 66 (8), 5377–5396. doi: 10.1021/acs.jmedchem.3c00134
  13. Cherfi M., Harit T., Yahyaoui M. I., Riahi A., Asehraou A., Malek F. J. Mol. Struct. 2022, 26, 1261, 132947,1261. doi: 10.1016/j.molstruc.2022.132947.
  14. Delius M., Geertsema E., Leigh D. Nature Chem. 2010, 2, 96–101. doi: 10.1038/nchem.481
  15. Delius M., Geertsema E.M., Leigh D.A., Tang D-T. D. J. Am. Chem. Soc. 2010, 132 (45), 16134–16145. doi: 10.1021/ja106486b
  16. Budagumpi S., Sathisha M.P., Kulkarni N.V., Kurdekar G.S., Revankar V.K. J. Incl. Phenom. Macrocycl. Chem. 2010, 66, 327–333. doi: 10.1007/s10847-009-9649-z
  17. Reddy P.M, Rohini R, Krishna E.R, Hu A, Ravinder V. Int. J. Mol. Sci. 2012, 13 (4), 4982–4992. doi: 10.3390/ijms13044982.
  18. Krishna E.R., Reddy P.M., Sarangapani M., Hanmanthu G., Geeta B., Rani K.Sh., Ravinder V. Spectrochim. Acta. Part A: Mol. Biomol. Spectroscopy. 2012, 97, 189–196. doi: 10.1016/j.saa.2012.05.073
  19. Rawat P., Singh R.N. Arab. J. Chem. 2019, 12 (7), 1219–1233. doi: 10.1016/j.arabjc.2014.10.050
  20. Jiang T., Tian H.-Q., Yu H.-H., Huang Ch., Zhu B.-X. Tetrahedron. 2023, 144, 133595. doi: 10.1016/j.tet.2023.133595
  21. Shu Zh., Sun Sh., Gu N., Yang Zh., Shang Y., Yang Yi, Xia M., Lin B., Yang P. Analyt. Chim. Acta. 2023, 1253, 341093. doi: 10.1016/j.aca.2023.341093
  22. Malek F., Harit T., Cherfi M., Kim B. Molecules. 2022, 27 (7), 2123–2149. doi: 10.3390/molecules27072123
  23. Amrhein J.A., Berger M. L., Balourdas D.I., Joerger A.C., Menge A., Kramer A., Frischkom J.M., Berger B.T., Elson L., Kaiser A., Schubert-Zsilavecz M., Muller S., Knapp S.K., Hanker T. J. Med. Chem. 2024, 67, 674–690. doi: 10.1021/acs.jmedchem3c01980
  24. Schuitema A.M., Aubel P.G., Koval I.A., Engelen M., Driessen W.L., Reedijk J., Lutz M., Spek A.L. Inorg. Chim. Acta. 2003, 355, 374–385. doi: 10.1016/S0020-1693(03)00362-1.
  25. Beeren S.R., Sanders J.K.M. Chem. Sci. 2011, 2, 1560–1567. doi: 10.1039/C1SC00168J
  26. Chio W.-I. K., Lee T.-Ch., Macrocycle‐Functionalised Nanosensors, Jenny Stanford Publishing, Singapore, 2024.
  27. Belda R., Pitarch-Jarque J., Soriano C., Llinares J.M., Blasco S., Ferrando-Soria J., García-Espan E. Inorg. Chem. 2013, 52 (19), 10795–10803. doi: 10.1021/ic400645t
  28. Laurent L., Pilar N., Carlos M., Vicente A.J., Carmen O., Francisco E., Enrique G-E. Julio L., Santiago L.V., Juan M.F. J. Am. Chem. Soc. 2001, 123, 10560–10570. doi: 10.1021/ja010956p.
  29. 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
  30. Zheng L.W., Xuan H.Z., Liu Y.R., Zhao B.X., Liu J.T., Miao J.Y. Helv. Chim. Acta. 2012, 95, 134–143. doi: 10.1002/hlca.201100249
  31. Харанеко А.О. ЖОрХ. 2016, 52, 1334–1337. [Kharaneko A.O. Russ. J. Org. Chem. 2016, 52, 1322–1325.] doi: 10.1134/S1070428016090128
  32. Mengeş N., Sari O., Abdullayev Y., Erdem S.S., Balci M., J. Org. Chem. 2013, 78 (11), 5184–5195. doi: 10.1021/jo4001228
  33. CrysAlisPro, version 1.171.38.41, Rigaku Oxford Diffraction, Oxford, 2015.
  34. Sheldrick G.M., Acta Crystallogr., Sect. A: Found. Adv. 2015, 71, 3–8. doi: 10.1107/S2053273314026370
  35. Sheldrick G.M., Acta Crystallogr., Sect. C: Struct. Chem. 2015, 71, 3–8. doi: 10.1107/S2053229614024218
  36. 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
  37. Granovsky A.A., Firefly, version 8, http://classic.chem.msu.su/gran/firefly/index.html.
  38. 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

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2. Scheme 1

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3. Scheme 2

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4. Scheme 3

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5. Scheme 4

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6. Scheme 5

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7. Scheme 6

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8. Fig. 1. Molecular structure of macrocyclic compound 7b according to X-ray diffraction data with atoms represented by thermal vibration ellipsoids with 50% probability.

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9. Fig. 2. Structure of 2 forms of compound 18 with a Ci-symmetric (a) and asymmetric (b) cycloconformer, according to quantum chemical calculation data.

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10. Content

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