Synthesis of Hexa-Substituted Benzene Derivative Based on 4-Pyridinecarboxaldehyde and Malononitrile

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Abstract

The present work reports the synthesis of a new compound 2-amino-4,6-di(pyridin-4-yl)benzene-1.3.5-tricarbonitrile as a result of the reaction of two moles of 2-(pyridin-4-ylmethylene)malononitrile with one mole of malononitrile in the presence of methylpiperazine as a catalyst. The structure of the obtained product was confirmed by NMR and X-ray. A plausible reaction mechanism is presented.

About the authors

I. G. Mamedov

Baku State University

Email: bsu.nmrlab@gmail.com
Az-1148 Baku, ul. Z. Khalilova, 23, Azerbaijan

F. N. Naghiyev

Baku State University

Email: bsu.nmrlab@gmail.com
Az-1148 Baku, ul. Z. Khalilova, 23, Azerbaijan

I. A. Yakushev

Kurnakov Institute of General and Inorganic Chemistry of RAS

Leninsky prosp., 31, Moscow, 119071 Russia

V. N. Khrustalev

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

ul. Miklukho-Maklaya, 6, Moscow, 117198 Russia; Leninsky prosp., 47, Moscow, 119991 Russia

References

  1. Freeman F. Chem. Rev. 1969, 69, 591–642. doi: 10.1021/cr60261a001
  2. Fatiadi A.J. Synthesis. 1978, 165–204. doi: 10.1055/s-1978-24703
  3. Wing L.K., Behanna H. A., Eldik L.J., Watterson D.M., Ralay R.H. Alzheimer Res. 2006, 3, 205–214. doi: 10.2174/156720506777632844
  4. Rozsa E., Obotka H., Nagy D, Farkas T., Saa K., Vec- sei L., Toldi J. Brain Res. Bull. 2008, 76, 474–479. doi: 10.1016/j.brainresbull.2007.12.001
  5. Odlo K., Hentzen J., Chabert J. F., Ducki S., Gani O.A. Sylte I., Skrede M., Florenes V.A., Hanse T.V. Bioorgan. Med. Chem. 2008, 16, 4829–4838. doi: 10.1016/j.bmc.2008.03.049
  6. Zhao H., Serby M.D., Xin Z., Szczepankiewicz B.G., Liu,M., Kosogof C., Liu L., Nelson T., Johnson E.F., Wang S., Terry P., Rebecca J.G., Jill E.C., Deanna L.H., Cele A.Z., Elizabeth H. F., Cristina R., James M.T., Hing L.S., Gang L. J. Med. Chem. 2006, 26, 4455–4458. doi: 10.1021/jm060465l
  7. Muranaka K., Sano A., Ichikawa S., Mastsuda A. Bioorgan. Med. Chem. 2008, 16, 5862–5870. doi: 10.1016/j.bmc.2008.04.070
  8. Burguete A., Pontiki D., Litina H., Villar R., Vicente E., Solano B., Ancizu S., Silanes S., Aldana I., Monge A. Bioorg. Med. Chem. Lett. 2007, 17, 6439–6443. doi: 10.1016/j.bmcl.2007.10.002
  9. Hirokawa Y., Kinoshita H., Tanaka T., Nakamura T., Fujimoto K., Kashimoto S., Kojima T., Kato S. Bioorg. Med. Chem. Lett. 2008, 18, 3556–3561. doi: 10.1016/j.bmcl.2008.05.011
  10. Palmer A.M., Grobbel B., Brehm C., Zimmermann P.J., Buhr W., Feth M.O., Holst H.C., Simon W.A. Bioorgan. Med. Chem. 2007, 15, 7647–7660. doi: 10.1016/j.bmc.2007.08.065
  11. Leon R., Rois C., Contelles J.M., Lopez M.G., Bar- cia, A.G., Villaroya M. Eur. J. Med. Chem. 2008, 43, 668–674. doi: 10.1016/j.ejmech.2007.06.001
  12. Mamedov I.G., Mamedova Y.V. Russ. J. Org. Chem. 2021, 57 (6), 942–949. doi: 10.1134/S1070428021060099
  13. Mamedov I.G., Shikhaliyeva I.M., Mamedova Y.V., Abdurahmanli S.G., Maharramov A.M. Indian J. Chem. 2019, 58B, 930–934.
  14. Rafat M.M., Amr S.A., Nermeen S.A. Anticanc. Agents Med. Chem. 2018, 17, 1951–1962. doi: 10.2174/1871520617666170725153523
  15. Amal A.A., Huda M. ACS Omega. 2020, 5, 10160–10166. doi: 10.1021/acsomega.0c01001
  16. Magerramov A.M., Naghiyev F.N., Mamedova G.Z., Asadov Kh.A., Mamedov I.G. Russ. J. Org. Chem. 2018, 54 (11), 1731–1734. doi: 10.1134/S1070428018110192
  17. Naghiyev F.N., Mamedov I.G., Asadov Kh.A., Dorovatovskii P.V., Khrustalev V.N., Maharramov A.M. Russ. J. Org. Chem. 2019, 55 (12), 1967–1970. doi: 10.1134/S1070428019120273
  18. Nesterov, V.N., Struchkov, Yu.T., Khoroshilov, G.E., Sharanin, Yu.A., Shklover, V.E., Russ. Chem. Bull. 1989, 38 (12), 2537. doi: 10.1007/BF00962440
  19. Maryasov M.A., Davydova V.V., Nasakin O.E., Shteingolts S.A., Lodochnikova O.A. Russ. J. Gen. Chem. 2020, 90 (8), 1573–1577. doi: 10.1134/S1070363220080289
  20. Khalilov A.N. Rev. Roum. de Chim. 2021, 66 (8–9), 719–723. doi: 10.33224/rrch.2021.66.8-9.04
  21. Askerov R.K., Maharramov A.M. Khalilov A.N., Ak- kurt M., Akobirshoeva A.A., Osmanov V.K., Borisov A.V. Acta Cryst. 2020, E76, 1007–1011. doi: 10.1107/S2056989020007033
  22. Rzayev R., Khalilov A. Chem. Rev. Lett. 2024, 7(3), 479–490. doi: 10.22034/crl.2024.465900.1371

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