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Synthesis and Properties of 4-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzenesulfonamide

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Abstract

The reaction of 4-aminobenzenesulfonamide with maleic anhydride gave (Z)-4-N-[4-(aminosulfonyl)phenyl)]amino-4-oxo-but-2-enoic acid, which was reacted with p-toluenesulfonic acid to obtain 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzenesulfonamide. The latter enters the aza-Michael reaction with secondary amines to form 4-[3-(N,N-dialkylamino)]-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrole-1-yl)benzenesulfonamides.

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REFERENCES

  1. Mikhailin, Yu.A., Termoustoichivye polimery i polimernye materialy (Heat-Resistant Polymers and Polymer Materials), St. Petersburg: Profession, 2006.

  2. Mitrasov, Yu.N., Kolyamshin, O.A., and Danilov, V.A., Maleinimidy: sintez, svoistva i polimery na ikh osnove (Maleimides: Synthesis, Properties and Polymers Based On Them), Cheboksary: Chuvash. Gos. Ped. Inst., 2017.

  3. Al-Suwaidan, I.A., Alanazi, A.M., El-Azab, A.S., Al-Obaid, A.M., ElTahir, K.E., Maarouf, A.R., ElEnin, M.A.A, and Alaa, A-M., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 9, p. 2601. https://doi.org/10.1016/j.bmcl.2013.02.107

    Article  CAS  PubMed  Google Scholar 

  4. Panov, A.A., Simonov, A.Y., Lavrenov, S.N., Lakatosh, S.A., and Trenin, A.S., Chem. Heterocycl. Compd., 2018, vol. 54, no. 2, p. 103. https://doi.org/10.1007/s10593-018-2240-z

    Article  CAS  Google Scholar 

  5. Patel, J.R. and Dholakiya, B.Z., Med. Chem. Res., 2012, vol. 21, no. 8, p. 1977. https://doi.org/10.1007/s00044-011-9718-x

    Article  CAS  Google Scholar 

  6. Ol’shevskaya, V.A., Makarenkov, A.V., Korotkova, N.S., Kononova, E.G., Konovalova, N.V., and Kalinin, V.N., Dokl. Chem., 2014, vol. 458, part 1, p. 165. https://doi.org/10.1134/s0012500814090018

    Article  Google Scholar 

  7. Patel, J.R., Dhorajiya, B.D., Dholakiya, B.Z., Badria, F.A., and Ibrahim, A.S., Med. Chem. Res., 2014, vol. 23, no. 8, p. 3907. https://doi.org/10.1007/s00044-014-0965-5

    Article  CAS  Google Scholar 

  8. Patel, J.R. and Dholakiya, B.Z., Res. Chem. Intermed., 2013, vol. 39, no. 9, p. 4159. https://doi.org/10.1007/s11164-012-0932-z

    Article  CAS  Google Scholar 

  9. SW Patent 583226, 1976; Ross. Zh. Khim., 1977, 14 O 131 P.

  10. JP Patent 30308, 1968; Ross. Zh. Khim., 1970, N 374 P.

  11. JP Patent 30313, 1968; Ross. Zh. Khim., 1970, 7 N 375 P.

  12. JP Patent 21433, 1968; Ross. Zh. Khim., 1969, 23 N 310 P.

  13. Ahmed, M., Qadir, M.A., Shafiq, M.I., Muddassar, M., Samra, Z.Q., and Hameed, A., Arab. J. Chem., 2019, vol. 12, no. 1, p. 41. https://doi.org/10.1016/j.arabjc.2016.11.017

    Article  CAS  Google Scholar 

  14. Gadad, A.K., Mahajanshetti, C.S., Nimbalkar, S., and Raichurkar, A., Eur. J. Med. Chem., 2000, vol. 35, no. 9, p. 853. https://doi.org/10.1016/S0223-5234(00)00166-5

    Article  CAS  PubMed  Google Scholar 

  15. Li, J.J., Anderson, G.D., Burton, E.G., Cogburn, J.N., Collins, J.T., Garland, D.J., Gregory, S.A., Huang, H-C., Isakson, P.C., Koboldt, C.M., Logusch, E.W., Norton, M.B., Perkins, W.E., Reinhard, E.J., Seibert, K., Veenhuizen, A.W., Zhang, Y., and Reitzt, D.B., J. Med. Chem., 1995, vol. 38, no. 22, p. 4570. https://doi.org/10.1021/jm00022a023

    Article  CAS  PubMed  Google Scholar 

  16. Wu, C., Decker, E.R., Holland, G.W., Brown, P.M., Stavros, F.D., Brock, T.A., and Dixon, R., Drugs Today, 2001, vol. 37, no. 7, p. 441. https://doi.org/10.1358/dot.2001.37.7.844187

    Article  CAS  Google Scholar 

  17. Ahmed, M., Qadir, M.A., Hameed, A., Arshad, M.N., Asiri, A.M., and Muddassar, M., Bioorg. Chem., 2018, vol. 76, p. 218. https://doi.org/10.1016/j.bioorg.2017.11.015

    Article  CAS  PubMed  Google Scholar 

  18. Cheng, M.-F., Hung, M.-S., Song, J.-S., Lin, S.-Y., Liao, F.-Y., Wu, M.-H., Hsiao, W., Hsieh, C.-L., Wu, J.-S., and Chao, Y.-S., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 3403. https://doi.org/10.1016/j.bmcl.2014.05.084

    Article  CAS  PubMed  Google Scholar 

  19. Wang, Z.-C., Duan, Y.-T., Qiu, H.-Y., Huang, W.-Y., Wang, P.-F., Yan, X.-Q., Zhang, S.-F., and Zhu, H.-L., RSC Adv., 2014, vol. 4, no. 62, p. 33029. https://doi.org/10.1039/C4RA03819C

    Article  CAS  Google Scholar 

  20. Kolyamshin, O.A., Danilov, V.A., Dashkova, G.Yu., and Kol’tsov, N.I., Russ. J. Org. Chem., 2005, vol. 41, no. 11, p. 1657. https://doi.org/10.1007/s11178-006-0014-z

    Article  CAS  Google Scholar 

  21. Kolyamshin, O.A., Danilov, V.A., and Kol’tsov, N.I., Russ. J. Org. Chem., 2007, vol. 43, no. 3, p. 393. https://doi.org/10.1134/S1070428007030104

    Article  CAS  Google Scholar 

  22. Kolyamshin, O.A., Mitrasov, Yu.N., Danilov, V.A., and Avruiskaya, A.A., Russ. J. Gen. Chem., 2019, vol. 89, no. 9, p. 1740. https://doi.org/10.1134/S1070363219090020

  23. Kolyamshin, O.A., Mitrasov, Yu.N., Danilov, V.A., and Avruiskaya, A.A., Russ. J. Gen. Chem., 2023, vol. 93, no. 2, p. 240. https://doi.org/10.1134/S1070363223020020

    Article  CAS  Google Scholar 

  24. Iannelli, M., Bezdushna, E., and Ritter, H., J. Macromol. Sci. A. Chem., 2007, vol. 44, no. 1, p. 7. https://doi.org/10.1080/10601320601041795

    Article  CAS  Google Scholar 

  25. Dhumad, A.M., Jassem, A.M., Alharis, R.A., and Almashal, F.A., J. Indian Chem. Soc., 2021, vol. 98, no. 4, p. 100055. https://doi.org/10.1016/j.jics.2021.100055

    Article  CAS  Google Scholar 

  26. SW Patent 598214, 1978; Ross. Zh. Khim., 1978, 23 N 157 P.

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This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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Authors and Affiliations

  1. Ul’yanov Chuvash State University, 428015, Cheboksary, Russia

    O. A. Kolyamshin, V. A. Danilov & Yu. Yu. Pyl’chikova

  2. Yakovlev Chuvash State Pedagogical University, 428000, Cheboksary, Russia

    Yu. N. Mitrasov & A. A. Avruyskaya

Authors
  1. O. A. Kolyamshin
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  2. Yu. N. Mitrasov
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  3. A. A. Avruyskaya
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  4. V. A. Danilov
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  5. Yu. Yu. Pyl’chikova
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Correspondence to O. A. Kolyamshin or Yu. N. Mitrasov.

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Kolyamshin, O.A., Mitrasov, Y.N., Avruyskaya, A.A. et al. Synthesis and Properties of 4-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzenesulfonamide. Russ J Gen Chem 93 (Suppl 2), S472–S477 (2023). https://doi.org/10.1134/S1070363223150082

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