NEW ASPECTS OF APPLICATION OF METHYL-4H-THIENO[3,2-b]PYRROLE-5-CARBOXYLATES AND DERIVATIVES IN SYNTHESIS. A REVIEW

Cover Page

Cite item

Full Text

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

Abstract

This review summarizes the results of the authors' study of chemical transformations of basic N-substituted methyl 4H-thieno[3,2-b]pyrrolecarboxylate in two main directions concerning the synthesis of new polymers and heterocycles (isoquinolines). In the first part presents data on the synthesis of a series of polyheterofunctionalized polymers based on the first developed from monomeric starting 4N-substituted bis-4H-thieno[3,2-b]-pyrrolomethanes and structurally similar products of cross-coupling (1H-pyrrol-3-ylmethyl)-4H-thieno[3,2-b]-pyrroles, their physicochemical properties were studied, possible step-by-step routes of formation and examples of practical use were proposed. In the second part the results obtained in the course of studying the AlCl3-promoted acylation reactions of N-benzyl- and N-2,3-dimethoxybenzyl-substituted methyl 4H-thieno[3,2-b]-pyrrole carboxylates with acid chlorides of the above-mentioned acids with the isolation of a new topology isoquinolines fused with 4H-thieno[3,2-b]pyrrole and benzene rings are discussed.

About the authors

S. A Torosyan

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences

Z. F Nurjakhmetova

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences

F. A Gimalova

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences

M. S Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences

Email: tsynth@anrb.ru

References

  1. Ching K.-Ch., Tran T.N.Q., Amrun S.N., Kam Y.-W., Ng L.F.P., Chai Ch.L.L.J. // J. Med. Chem. 2017. V. 60. P. 3165–3186. https://doi.org/10.1021/acs.jmedchem.7b00180
  2. Zhang X., Yan J., Wang H., Wang Y., Wang J., Zhao D.J. // Biomol. Struct. Dyn. 2021. V. 39. № 4. P. 1189–1202. https://doi.org/10.1080/07391102.2020.1726819
  3. Нуриахметова З.Ф. Синтез и превращения производных метил 4H-тиено[3.2-b]пиррол-5-карбоксилата. Автореф. дис. ... канд. хим. наук. Уфа, 2023. 22 с.
  4. Sartori L., Mercurio C., Amigoni F., Cappa A., Faga G., Fattori R., Legnaghi E., Ciossani G., Mattevi A., Meroni G., Moretti L., Cecatiello V., Pasqualato S., Romussi A., Thaler F., Trifiro P., Villa M., Vultaggio S., Botrugno O.A., Dessanti P., Minucci S., Zagarri E., Carettoni D., Iuzzolino L., Varasi M., Vianello P. // J. Med. Chem. 2017. V. 60. P. 1673–1692. https://doi.org/10.1021/acs.jmedchem.6b01018
  5. Arias A.C., MacKenzie J.D., McCulloch I., Rivnay J., Salleo A. // Chem. Rev. 2010. V. 110. P. 3–24. https://doi.org/10.1021/cr900150b
  6. Torosyan S.A., Zagitov V.V., Gimalova F.A., Biglova R.Z., Mifakhov M.S. // Mendeleev Commun. 2018. V. 28. P. 192–194. https://doi.org/10.1016/j.mencom.2018.03.028
  7. Торосян С.А., Нуриахметова З.Ф., Гималова Ф.А., Мифтахов М.С. // ЖОрХ. 2019. Т. 55. С. 1921–1925. https://doi.org/10.1134/S0514749219120164
  8. Mifakhov M.S., Torosyan S.A., Gimalova F.A., Khursan S.L., Nurjakhmetova Z.F., Shchurik E.V., Kruevaya O.A., Shestakov A.F., Troshin P.A. // Polym. Chem. 2023. V. 14. P. 4986–4893. https://doi.org/10.1039/d3py00893b
  9. Habermas K.L., Denmark S., Jones T.K. // Org. React. 1994. V. 45. P. 1–158. https://doi.org/10.1002/0471264180.or045.01
  10. Pellissier H. // Tetrahedron. 2005. V. 61. P. 6479–6517. https://doi.org/10.1016/j.tet.2005.04.014
  11. Bentley K.W. // Nat. Prod. Rep. 2006. V. 23. P. 444–463. https://doi.org/10.1039/B509523A
  12. Khan A.Y., Suresh Kumar G. // Biophys. Rev. 2015. V. 7. P. 407–420. https://doi.org/10.1007/s12551-015-0183-5
  13. Heterocycles in natural product synthesis. Majumdar K.C., Chattopadhyay S.K. (eds.). Weinheim: Wiley, 2011. 658 p.
  14. Shuai S., MaoJ., Zhou F., Yan Q., Chen L., LiJ., Walsh P.J., Liang G. // J. Org. Chem. 2024. V. 89. P. 6793–6797. https://doi.org/10.1021/acs.joc.4c00123
  15. Nevskaya A.A., Mifyakhova A.R. // Chem. Heterocycl. Compd. 2019. V. 55. P. 193–195. https://doi.org/10.1007/s10593-019-02439-z
  16. Fodor G., Nagubar S. // Tetrahedron. 1980. V. 36. P. 1279–1300. https://doi.org/10.1016/0040-4020(80)85039-3
  17. Gensler W.J. // Organic Reactions. New York: Wiley, 1951. V. 6. P. 191–205.
  18. Cox E.D., Cook J.M. // Chem. Rev. 1995. V. 95. P. 1797–1842. https://doi.org/10.1021/cr00038a004
  19. Torosyan S.A., Nurjakhmetova Z.F., Gimalova F.A., Lobov A.N., Mifakhov M.S. // Russ. J. Gen. Chem. 2025. V. 95. № 5. P. 1204–1209. https://doi.org/10.1134/S1070363225601395

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

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).