Skip to main content
Log in

Synthesis of 1,3-dihydro-2H-benzimidazol-2-ones (microreview)

  • HETEROCYCLES IN FOCUS
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This microreview covers data regarding the synthesis of 1,3-dihydro-2H-benzimidazol-2-ones published during the last five years. The synthetic routes to benzimidazolones can be classified into several types: cyclocarbonylation of 1,2-diaminobenzenes, transformation of benzimidazolium salts, synthesis from arylureas, a Curtius reaction of anthranilic acids or phthalic anhydrides, and other pathways.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Abbas, M. A.; Hameed, S.; Farman, M.; Kressler, J.; Mahmood, N. Bioconjug. Chem. 2015, 26, 120.

    Article  CAS  Google Scholar 

  2. (a) Gondal, H. Y.; Ali, M. J. Chem. Soc. Pak. 2013, 35, 1343. (b) Xu, N.; Yang, C.; Gan, X.; Wei, S.; Ji, Z. Int. J. Mol. Sci. 2013, 14, 6790.

  3. Patel, V.; Bhatt, N.; Bhatt, P.; Joshi, H. D. Med. Chem. Res. 2014, 23, 2133.

    Article  CAS  Google Scholar 

  4. Zeng, Q.; Rosenblum, S. B.; Yang, Z.; Jiang, Y.; McCormick, K. D.; Aslanian, R. G.; Duguma, L.; Kozlowski, J. A.; Shih, N.-Y.; Hey, J. A.; West, R. E.; Korfmacher, W. A.; Berlin, M.; Boyce, C. W. Bioorg. Med. Chem. Lett. 2013, 23, 6001.

    Article  CAS  Google Scholar 

  5. Sun, Y.; Pandit, B.; Chettiar, S. N.; Etter, J. P.; Lewis, A.; Johnsamuel, J.; Li, P.-K. Bioorg. Med. Chem. Lett. 2013, 23, 4465.

    Article  CAS  Google Scholar 

  6. (a) Ullah, N. J. Enzyme Inhib. Med. Chem. 2014, 29, 281. (b) Xu, Y.-L.; Lin, H.-Y.; Ruan, X.; Yang, S.-G.; Hao, G.-F.; Yang, W.-C.; Yang, G.-F. Eur. J. Med. Chem. 2015, 92, 427. (c) Fukaya, T.; Kodo, T.; Ishiyama, T.; Nishikawa, H.; Baba, S.; Masumoto, S. Bioorg. Med. Chem. 2013, 21, 1257. (d) Bonuga, Y. R.; Nath, A. R. Pharma Chem. 2012, 4, 2396. (e) Liu, W.; Lau, F.; Liu, K.; Wood, H. B.; Zhou, G.; Chen, Y.; Li, Y.; Akiyama, T. E.; Castriota, G.; Einstein, M.; Wang, C.; McCann, M. E.; Doebber, T. W.; Wu, M.; Chang, C. H.; McNamara, L.; McKeever, B.; Mosley, R. T.; Berger, J. P.; Meinke, P. T. J. Med. Chem. 2011, 54, 8541.

  7. Bruncko, M.; Tahir, S. K.; Song, X.; Chen, J.; Ding, H.; Huth, J. R.; Jin, S.; Judge, R. A.; Madar, D. J.; Park, C. H.; Park, C.-M.; Petros, A. M.; Tse, C.; Rosenberg, S. H.; Elmore, S. W. Bioorg. Med. Chem. Lett. 2010, 20, 7503.

    Article  CAS  Google Scholar 

  8. (a) Bouaziz, O.; Amari, M.; Bachar, R.; Khier, N.; Fodili, M.; Almeida Paz, F. A.; Talhi, O.; Silva, A. M. S. Tetrahedron Lett. 2015, 56, 1020. (b) Rasheed, M. A.; Shaik, N. M.; Nirogi, R. Synth. Commun. 2013, 43, 1796.

  9. (a) Maisuradze, M. G.; Ananiashvili, V. O.; Alapishvili, M. G.; Gakhokidze, N. Z.; Matnadze, M. M.; Palavandishvili, G. A. Chem. Heterocycl. Compd. 2013, 48, 1801. [Khim. Geterotsikl. Soedin. 2012, 1924.] (b) Yao, J.-L.; Gao, X.; Sun, W.; Shi, S.; Yao, T.-M. Dalton Trans. 2013, 42, 5661. (c) Abbas, M. A.; Hameed, S.; Kressler, J. Asian J. Chem. 2013, 25, 509.

  10. Yu, B.; Zhang, H.; Zhao, Y.; Chen, S.; Xu, J.; Hao, L.; Liu, Z. ACS Catal. 2013, 3, 2076.

    Article  CAS  Google Scholar 

  11. Kamata, K.; Kimura, T.; Sunaba, H.; Mizuno, N. Catal. Today 2014, 226, 160.

    Article  CAS  Google Scholar 

  12. Troisi, L.; Granito, C.; Perrone, S.; Rosato, F. Tetrahedron Lett. 2011, 52, 4330.

    Article  CAS  Google Scholar 

  13. Jing, Y.; Liu, R.; Lin, Y.; Zhou, X. Sci. China Chem. 2014, 57, 1117.

    Article  CAS  Google Scholar 

  14. Dekhane, D. V.; Pawar, S. S.; Gupta, S. V.; Shingare, M. S.; Thore, S. N. Lett. Org. Chem. 2011, 8, 406.

    Article  CAS  Google Scholar 

  15. Ryu, K. E.; Kim, B. R.; Sung, G. H.; Yoon, H. J.; Yoon, Y.-J. Synlett 2015, 26, 1985.

    Article  CAS  Google Scholar 

  16. Andreoli, F.; Kaid-Slimane, R.; Coppola, F.; Farran, D.; Roussel, C.; Vanthuyne, N. J. Org. Chem. 2015, 80, 3233.

    Article  CAS  Google Scholar 

  17. Li, J.-P.; Huang, Y.; Xie, M.-S.; Qu, G.-R.; Niu, H.-Y.; Wang, H.-X.; Qin, B.-W.; Guo, H.-M. J. Org. Chem. 2013, 78, 12629.

    Article  CAS  Google Scholar 

  18. Manjare, S. T.; Sharma, S.; Singh, H. B.; Butcher, R. J. J. Organomet. Chem. 2012, 717, 61.

    Article  CAS  Google Scholar 

  19. Lima, H. M.; Lovely, C. J. Org. Lett. 2011, 13, 5736.

    Article  CAS  Google Scholar 

  20. Orlov, M. A.; Kapitanov, I. V; Korotkikh, N. I.; Shvaika, O. P. Chem. Heterocycl. Compd. 2014, 50, 111. [Khim. Geterotsikl. Soedin. 2014, 123.]

  21. Ernst, J. B.; Tay, N. E. S.; Jui, N. T.; Buchwald, S. L. Org. Lett. 2014, 16, 3844.

    Article  CAS  Google Scholar 

  22. Berry, J. F.; Ferraris, D. V; Duvall, B.; Hin, N.; Rais, R.; Alt, J.; Thomas, A. G.; Rojas, C.; Hashimoto, K.; Slusher, B. S.; Tsukamoto, T. ACS Med. Chem. Lett. 2012, 3, 839.

    Article  CAS  Google Scholar 

  23. (a) Shtamburg, V. G.; Shishkin, O. V; Shtamburg, V. V; Zubatyuk, R. I.; Mazepa, A. V.; Kostyanovsky, R. G. Chem. Heterocycl. Compd. 2013, 49, 1195. [Khim. Geterotsikl. Soedin. 2013, 1282.] (b) Shtamburg, V. G.; Tsygankov, A. V.; Gerasimenko, M. V.; Shishkin, O. V.; Zubatyuk, R. I.; Mazepa, A. V.; Kostyanovsky, R. G. Mendeleev Commun. 2011, 21, 50.

  24. Yu, J.; Gao, C.; Song, Z.; Yang, H.; Fu, H. Eur. J. Org. Chem. 2015, 5869.

  25. Beyer, A.; Reucher, C. M. M.; Bolm, C. Org. Lett. 2011, 13, 2876.

    Article  CAS  Google Scholar 

  26. Deau, E.; Robin, E.; Voinea, R.; Percina, N.; Satała, G.; Finaru, A.-L.; Chartier, A.; Tamagnan, G.; Alagille, D.; Bojarski, A. J.; Morisset- Lopez, S.; Suzenet, F.; Guillaumet, G. J. Med. Chem. 2015, 58, 8066.

    Article  CAS  Google Scholar 

  27. López, H. S.; Enciso, J. E.; Ochoa-Terán, A.; Velazquez, J. I.; Sarmiento, J. I. Mendeleev Commun. 2016, 26, 69.

    Article  Google Scholar 

  28. Zeng, R.; Chen, P. H.; Dong, G. ACS Catal. 2016, 6, 969.

    Article  CAS  Google Scholar 

  29. Liu, H.; Tang, J.; Jiang, L.; Zheng, T.; Wang, X.; Lv, X. Tetrahedron Lett. 2015, 56, 1624.

    Article  CAS  Google Scholar 

  30. Mamedov, V. A.; Zhukova, N. A.; Beschastnova, T. N.; Syakaev, V. V.; Krivolapov, D. B.; Mironova, E. V.; Zamaletdinova, A. I.; Rizvanov, I. K.; Latypov, S. K. J. Org. Chem. 2015, 80, 1375.

    Article  CAS  Google Scholar 

  31. Mamedov, V. A.; Zhukova, N. A.; Zamaletdinova, A. I.; Beschastnova, T. N.; Kadyrova, M. S.; Rizvanov, I. K.; Syakaev, V. V; Latypov, S. K. J. Org. Chem. 2014, 79, 9161.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Juan I. Sarmiento-Sánchez.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(12), 1002–1004

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Armenta, R., Sarmiento-Sánchez, J.I. Synthesis of 1,3-dihydro-2H-benzimidazol-2-ones (microreview). Chem Heterocycl Comp 52, 1002–1004 (2016). https://doi.org/10.1007/s10593-017-1999-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-1999-7

Keywords

Navigation