Synthesis of 1,5-Diaryl-Substituted 2-(2-Oxo-1,2-Dihydro-3H-Pyrrol-3-Ylidene)Malononitriles

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

Previously unknown cyano-substituted derivatives of pyrrol-2-one containing a 1,5-diaryl fragment in their structure have been synthesized. Their preparation is based on the initial reaction of enamines with oxalyl chloride, leading to intermediate pyrrol-2,3-diones, which then react with malononitrile to form the final products.

About the authors

S. A Blinov

Chuvash State University named after I.N. Ulyanov

ORCID iD: 0009-0009-9001-6033
Cheboksary,Russia

A. G Milovidova

Chuvash State University named after I.N. Ulyanov

ORCID iD: 0000-0001-8475-6419
Cheboksary, Russia

M. Yu Belikov

Chuvash State University named after I.N. Ulyanov

Email: belikovmil@mail.ru
ORCID iD: 0000-0001-6444-3810
Cheboksary, Russia

References

  1. Ghuge R.B., Khadse A.N. Vicinal Diaryl Substituted Heterocycl. 2018, 47–82. https://doi.org/10.1016/B978-0-08-102237-5.00003-1
  2. Ramajayam R. Eur. J. Med. Chem. 2019, 162, 1–17. https://doi.org/10.1016/j.ejmech.2018.10.054
  3. Ganesh B.H., Raj A.G., Aruchamy B., Nanjan P., Drago C., Ramani P. ChemMedChem. 2023, 19. https://doi.org/10.1002/cmdc.202300447
  4. Saletti M., Maramai S., Reale A., Paolino M., Brogi S., Di Capua A., Cappelli A., Giorgi G., D’Avino D., Rossi A., Ghelardini C., Di Cesare Mannelli L., Sardella R., Carotti A., Woelkart G., Klösch B., Bigogno C., Dondio G., Anzini M. Eur. J. Med. Chem. 2022, 241, 114615. https://doi.org/10.1016/j.ejmech.2022.114615
  5. Biava M., Porretta G.C., Poce G., Supino S., Forli S., Rovini M., Cappelli A., Manetti F., Botta M., Sautebin L., Rossi A., Pergola C., Ghelardini C., Vivoli E., Makovec F., Anzellotti P., Patrignani P., Anzini M. J. Med. Chem. 2007, 50, 5403–5411. https://doi.org/10.1021/jm0707525
  6. Venditti G., Poce G., Consalvi S., Biava M. Chem. Heterocycl. Compd. 2017, 53, 281–291. https://doi.org/10.1007/s10593-017-2050-8
  7. Biava M., Porretta G.C., Poce G., Battilocchio C., Alfonso S., Logu A.D., Serra N., Manetti F., Botta M. Bioorg. Med. Chem. 2010, 18, 8076–8084. https://doi.org/10.1016/j.bmc.2010.09.006
  8. Biava M., Porretta G.C., Poce G., Supino S., Deidda D., Pompei R., Molicotti P., Manetti F., Botta M. J. Med. Chem. 2006, 49, 4946–4952. https://doi.org/10.1021/jm0602662
  9. Sun J., Chen L., Liu C., Wang Z., Zuo D., Pan J., Qi H., Bao K., Wu Y., Zhang W. Chem. Biol. Drug. Des. 2015, 86, 1541–1547. https://doi.org/10.1111/cbdd.12617
  10. Masci D., Hind C., Islam M.K., Toscani A., Clifford M., Coluccia A., Conforti I., Toutuot M., Memdouth S., Wei X., La Regina G., Silvestri R., Sutton J.M., Castagnolo D. Eur. J. Med. Chem. 2019, 178, 500–514. https://doi.org/10.1016/j.ejmech.2019.05.087
  11. Xiang H., Liu R., Zhang X., An R., Zhou M., Tan C., Li Q., Su M., Guo C., Zhou L., Li Y., Wang R. J. Med. Chem. 2023, 66, 2457-2476. https://doi.org/10.1021/acs.jmedchem.2c01233
  12. Bassetto M., Leyssen P., Neyts J., Yerukhimovich M.M., Frick D.N., Brancale A. Bioorg. Med. Chem. Lett. 2017, 27, 936-940. https://doi.org/10.1016/j.bmcl.2016.12.087
  13. Cosner C.C., Markiewicz J.T., Bourbon P., Mariani C.J., Wiest O., Rujoi M., Rosenbaum A.I., Huang A.Y., Maxfield F.R., Helquist P. J. Med. Chem. 2009, 52, 6494-6498. https://doi.org/10.1021/jm900707n
  14. Salem M.A., Ragab A., Askar A.A., El-Khalafawy A., Makhlouf A.H. Eur. J. Med. Chem. 2020, 188, 111977. https://doi.org/10.1016/j.ejmech.2019.111977
  15. Woodard C.L., Li Z., Kathcart A.K., Terrell J., Gerena L., Lopez-Sanchez M., Kyle D.E., Bhattacharjee A.K., Nichols D.A., Ellis W., Prigge S.T., Geyer J.A., Waters N.C. J. Med. Chem. 2003, 46, 3877-3882. https://doi.org/10.1021/jm0300983
  16. Chu W., Rothfuss J., Zhou D., Mach R.H. Bioorg. Med. Chem. Lett. 2011, 21, 2192-2197. https://doi.org/10.1016/j.bmcl.2011.03.015
  17. El-Sharief A.M.S., Ammara Y.A., Belal A., El-Sharief M.A.M.Sh., Mohamed Y.A., Mehany A.B.M., Elhag Ali G.A.M., Ragab A. Bioorg. Chem. 2019, 85, 399-412. https://doi.org/10.1016/j.bioorg.2019.01.016
  18. Belikov M.Yu., Milovidova A.G., Ievlev M.Yu., Fedoseev S.V. Org. Biomol. Chem. 2024, 22, 4757-4765. https://doi.org/10.1039/d4ob00612g
  19. Milovidova A.G., Belikov M.Yu., Ievlev M.Yu., Nasakin O.E., Ershov O.V., Tafeenko V.A. Synth. Commun. 2021, 51, 727-737. https://doi.org/10.1080/00397911.2020.1852434
  20. Belikov M.Yu., Milovidova A.G., Ievlev M.Yu. New J. Chem. 2022, 46, 11030-11034. https://doi.org/10.1039/d2nj01658c
  21. Cobas A., Guitian E., Castedo L. J. Org. Chem. 1993, 58, 3113-3117. https://doi.org/10.1021/jo00063a034
  22. Sano T., Horiguchi Y., Toda J., Imafuku K., Tsuda Y. Chem. Pharm. Bull. 1984, 32, 497-503. https://doi.org/10.1248/cpb.32.497

Supplementary files

Supplementary Files
Action
1. JATS XML

Copyright (c) 2025 Russian Academy of Sciences

Согласие на обработку персональных данных

 

Используя сайт https://journals.rcsi.science, я (далее – «Пользователь» или «Субъект персональных данных») даю согласие на обработку персональных данных на этом сайте (текст Согласия) и на обработку персональных данных с помощью сервиса «Яндекс.Метрика» (текст Согласия).