Skip to main content
Log in

Synthesis of 1,2-Diazepines by the Bischler–Napieralski Reaction

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript


A new strategy has been proposed for the synthesis of 5H-[1]benzofuro[2,3-d][1,2]diazepines containing two aryl substituents in the diazepine fragment. The key stage of the synthesis is intramolecular cyclization of the corresponding hydrazides under the Bischler–Napieralski reaction conditions.

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


  1. O’Neill, M.J. and Witkin, J.M., Curr. Drug Targets, 2007, vol. 8, p. 603.

    Article  PubMed  Google Scholar 

  2. Lynch, G. and Gall, C.M., Trends Neurosci., 2006, vol. 29, p. 554.

    Article  CAS  PubMed  Google Scholar 

  3. Lynch, G., Curr. Opin. Pharmacol., 2004, vol. 4, p. 4.

    Article  CAS  PubMed  Google Scholar 

  4. Grigor’ev, V.V., Proshin, A.N., Kinzirsky, A.S., and Bachurin, S.O., Russ. Chem. Rev., 2009, vol. 78, p. 485.

    Article  CAS  Google Scholar 

  5. Szenazi, G. and Harsing, L.G., Drug Discovery Today: Ther. Strategies, 2004, vol. 1, p. 69.

    Article  CAS  Google Scholar 

  6. Sólyom, S. and Tarnawa, I., Curr. Pharm. Des., 2002, vol. 8, p. 913.

    Article  PubMed  Google Scholar 

  7. Chimirri, A., De Sarro, G., Quartarone, S., Barreca, M.L., Caruso, R., De Luca, L., and Gitto, R., Pure Appl. Chem., 2004, vol. 76, p. 931.

    Article  CAS  Google Scholar 

  8. Tarnawa, I., Farkas, S., Berzsenyi, P., Pataki, A., and Andrasi, F., Eur. J. Pharmacol., 1989, vol. 167, p. 193.

    Article  CAS  PubMed  Google Scholar 

  9. De Sarro, A., De Sarro, G., Gitto, R., Grasso, S., Micale, N., Quartarone, S., and Zappala, M., Bioorg. Med. Chem. Lett., 1998, vol. 8, p. 971.

    Article  PubMed  Google Scholar 

  10. Sizonenko, E.S., Kobrakov, I.K., Popov, V.Yu., Suikov, S.Yu., and Bogza, S.L., Chem. Heterocycl. Compd., 2013, vol. 49, p. 1352.

    Article  CAS  Google Scholar 

  11. Wang, J., Wang, L., Guo, S., Zha, S., and Zhu, J., Org. Lett., 2017, vol. 19, p. 3640.

    Article  CAS  PubMed  Google Scholar 

  12. Espahbodini, M., Ettari, R., Wen, W., Wu, A., Shen, Y.-C., Niu, L., Grasso, S., and Zappalà, M., Bioorg. Med. Chem., 2017, vol. 25, p. 3631.

    Article  CAS  Google Scholar 

  13. Tolkunov, V.S., Eresko, A.B., Khizhan, A.I., Shishkin, O.V., Palamarchuk, G.V., and Tolkunov, S.V., Chem. Heterocycl. Compd., 2009, vol. 45, p. 726.

    Article  CAS  Google Scholar 

  14. Eresko, A.B., Tolkunov, V.S., and Tolkunov, S.V., Chem. Heterocycl. Compd., 2010, vol. 46, p. 1127.

    Article  CAS  Google Scholar 

  15. Eresko, A., Tolkunov, V., and Tolkunov, S., Monatsh. Chem., 2011, vol. 142, p. 931.

    Article  CAS  Google Scholar 

  16. Tolkunov, V.S., Eresko, A.B., Mazepa, A.V., and Tolkunov, S.V., Chem. Heterocycl. Compd., 2011, vol. 47, p. 1170.

    Article  CAS  Google Scholar 

  17. Voskresensky, L.G., Borisova, T.N., Babakhanova, M.I., Chervyakova, T.M., Titov, A.A., Butin, A.V., Nevolina, T.A., Khrustalev, V.N., and Varlamov, A.V., Chem. Heterocycl. Compd., 2013, vol. 49, p. 1024.

    Article  CAS  Google Scholar 

  18. Cobo, J., Nogueras, M., Low, J.N., and Rodríguez, R., Tetrahedron Lett., 2008, vol. 49, p. 7271.

    Article  CAS  Google Scholar 

  19. Fu, R., Xu, X., Dang, Q., and Bai, X., J. Org. Chem., 2005, vol. 70, p. 10 810.

    Article  CAS  Google Scholar 

  20. El-Kashef, H., Rathelot, P., Vanelle, P., and Rault, S., Monatsh. Chem., 2007, vol. 138, p. 469.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to A. B. Eresko.

Additional information

Original Russian Text © A.V. Muratov, S.A. Grebenyuk, A.B. Eresko, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 6, pp. 860–864.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Muratov, A.V., Grebenyuk, S.A. & Eresko, A.B. Synthesis of 1,2-Diazepines by the Bischler–Napieralski Reaction. Russ J Org Chem 54, 861–866 (2018).

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: