Reaction of substituted chalcone with guanidine in the presence of hydrogen peroxide

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription or Fee Access

Abstract

This work reports the synthesis of a new compound 3 as a result of the reaction (2E)-1-(4-bromophenyl)-3-[5-bromo-2-(prop-2-en-1-yloxy)phenyl]prop-2-en-1-one with guanidine in the presence of hydrogen peroxide. The structure of the resulting product was confirmed by NMR spectroscopy and X-ray diffraction. A probable reaction mechanism is presented.

Full Text

Restricted Access

About the authors

I. G. Mamedov

Baku State University

Author for correspondence.
Email: bsu.nmrlab@gmail.com
ORCID iD: 0000-0002-5757-9899

Химический факультет

Azerbaijan, ul. Z. Khalilov, 23, Baku, Az-1148

V. N. Khrustalev

Peoples’ Friendship University of Russia (RUDN University); N.D. Zelinsky Institute of Organic Chemistry RAS

Email: bsu.nmrlab@gmail.com
ORCID iD: 0000-0001-8806-2975
Russian Federation, ul. Miklukho-Maklaya, 6, Moscow, 117198 ; Leninsky prosp., 47, Moscow, 119991

References

  1. Mamedov I.G., Naghiyev F.N., Maharramov A.M., Uwangue O., Farewell A., Sunnerhagen P., Erdelyi M. Mendeleev Commun., 2020, 30, 498–499. doi: 10.1016/j.mencom.2020.07.031
  2. Mamedov I.G., Khrustalev V.N., Doravotovskii P.V., Naghiyev F.N., Maharramov A.M. Mendeleev Commun., 2019, 29, 232–233. doi: 10.1016/j.mencom.2019.03.040
  3. Mamedov I.G., Mamedova Y.V. Indian J. Chem., 2021, 60B, 283–86.
  4. Naghiyev F.N., Mamedov I.G., Khrustalyev V.N., Shixaliyev N.G., Maharramov A.M. J. Chinese Chem. Soc., 2019, 66 (3), 253–256. doi: 10.1002/jccs.201800283
  5. Mamedov I.G., Mamedova Y.V. Russ. J. Org. Chem., 2021, 57 (6), 942–949. doi: 10.1134/S1070428021060099
  6. Mamedova Y.V., Hasanova A.E., Gasimova Sh.Z., Huseynova R.A., Mamedov I.G. New Materials, Compd. Applicat., 2020, 4, 16–19.
  7. Mamedov I.G., Shikhaliyeva I.M., Mamedova Y.V., Abdurahmanli S.G., Maharramov A.M. İndian J. Chem., 2019, 58B, 930–934.
  8. Khalilov A.N., Cisterna J., Cárdenas A., Tuzun B., Erkan S., Gurbanov A.V., Brito I. J. Mol. Struct., 2024, 1313, 138652. doi: 10.1016/j.molstruc.2024.138652
  9. Naghiyev F.N., Pavlov A.V., Khrustalev V.N., Akkurt M., Khalilov A.N., Akobirshoeva A.A., Mamedov I.G.. Acta Cryst. 2021, E77, 930–934. doi: 10.1107/S2056989021007994
  10. Naghiyev F.N., Tereshina T.A., Khrustalev V.N., Akkurt M., Khalilov A.N., Akobirshoeva A.A., Mamedov I.G.. Acta Cryst. 2021, E77, 512–515. doi: 10.1107/S2056989021003625
  11. Antonova M.M., Baranov V.V., Kravchenko, A.N. Chem. Heterocycl. Compd., 2015, 51, 395–420. doi: 10.1007/s10593-015-1716-3
  12. Keel K.L., Tepe J.J. Org. Chem. Front., 2020, 7, 3284–3311. doi: 10.1039/D0QO00764A
  13. Ahmed K., Ramakrishna G., Raju P., Viswanath A., Janaki M.R., Balakishan G., Pal-Bhadra Manika. Bioorg. Med. Chem. Lett., 2010, 20, 4865–4869. doi: 10.1016/j.bmcl.2010.06.097
  14. Janaki R.M., Pushpavalli S.N.C.V.L., Rama K.G., Sarma P., Debasmita M., Ahmed K., Utpal B., Pal Bhadra M. Canc. Cell Inter., 2011, 11 (11), 1–12. doi: 10.1186/1475-2867-11-11
  15. Аnitha S., Usha R.P., Prameela S.N.J. Med. Chem. Res., 2015, 24, 851–859. doi: 10.1007/s00044-014-1179-6
  16. Navin B.P., Hemant R.P. J. Heterocycl. Chem., 2011, 48 (2), 373–380. doi: 10.1002/jhet.588
  17. Bassyouni F., Tarek M., Salama A., Ibrahim B., Dine S.S.E., Yassin N., Hassanein A., Moharam M., Abdel-Rehim M. Molecules, 2021, 26, 2370–2390. doi: 10.3390/molecules26082370
  18. Yang X., Deng M., Zhang X., Wang Y., Song K., Cong R., Meng L., Zhang J. Chem. Biol. Drug Des., 2019, 94 (6), 2013–2022. doi: 10.1111/cbdd.13425
  19. El-Sharkawy K.A., AlBratty M.M., Alhazmi H.A. Brazil. J. Pharm. Sci., 2018, 54 (4), 1–13. doi: 10.1590/s2175-97902018000400153
  20. Jain K.S., Arya N., Inamdar N.N., Auti P.B., Unawane S.A., Puranik H.H., Sanap M.S., Inamke A.D., Mahale V.J., Prajapati C.S., Shishoo C.J. Curr. Topics Med. Chem., 2016, 16, 3133–3174. doi: 10.2174/1568026616666160609100410
  21. Sharma V., Chitranshi N., Agarwal A.K. Int. J. Med. Chem., 2014, 1–32. doi: 10.1155/2014/202784
  22. Kumar R., Arora J., Prasad A.K., Islam N., Verma A.K. Med. Chem. Res., 2013, 22, 5624–5631. doi: 10.1007/s00044-013-0555-y
  23. Samshuddin S., Narayana B., Sarojini B.K., Yathirajan H.S., Raghavendra R. Pharma Chemica, 2012, 4 (4), 1445–1457.
  24. Mamedov I.G., Khrustalev V.N. Russ. J. Org. Chem., 2023, 59 (9), 1637–1640. doi: 10.1134/S1070428023090245

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Fig. 1. The structure of the molecule of compounds 1 and 2 according to X-ray diffraction data

Download (119KB)
Indexing metadata
3. Fig. 2. The structure of the molecule of compound 3 according to X-ray diffraction data

Download (89KB)
Indexing metadata
4. Scheme

Download (112KB)
Indexing metadata
5. Content

Download (47KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences