Skip to main content
SpringerLink
Log in

Synthesis of N-alkylated benzo- and pyridothienopyrrolo-[1,2a][1,4]diazepin-6-ones acting as antidotes against the herbicide 2,4-D

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

We report N-alkylation reactions of pyrrolo[1,2-a][1,4]diazepin-6-ones annulated with a benzene ring or thieno[2,3-b]pyridine system. A range of new N5-substituted pyrrolodiazepines were synthesized, including compounds acting as antidotes against the herbicide 2,4-D.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 2

Similar content being viewed by others

References

  1. (a) Ramajayam, R.; Girdhar, R.; Yadav, M. R. Mini Rev. Med. Chem. 2007, 7, 793. (b) Fotso, S. Mini Rev. Org. Chem. 2010, 7, 68. (c) Kaur, N. Int. J. Pharm. Bio. Sci. 2013, 4(2), 318.

  2. Stroganova, T.; Vasilin, V.; Butin, A.; Nevolina, T.; Krapivin, G. Synlett 2007, 1106.

  3. Stroganova, T. A.; Red'kin, V. M.; Vasilin, V. K.; Krapivin, G. D. J. Heterocycl. Chem. 2013, 50, 854.

    Article  CAS  Google Scholar 

  4. Red'kin, V. M.; Stroganova, T. A.; Vasilin, V. K.; Krapivin, G. D. Chem. Heterocycl. Compd. 2012, 47, 1319. [Khim. Geterotsikl. Soedin. 2011, 1588].

  5. (a) Stroganova, T. A.; Vasilin, V. K.; Zelenskaya, E. A.; Red'kin, V. M.; Krapivin, G. D. Synthesis 2008, 19, 3088. (b) Butin, A. V.; Nevolina, T. A.; Shcherbinin, V. A.; Trushkov, I. V.; Cheshkov, D. A.; Krapivin, G. D. Org. Biomol. Chem. 2010, 8, 3316.

  6. a) Beccalli, E. M.; Broggini, G.; Paladino, G.; Zoni, C. Tetrahedron 2005, 61, 61. (b) Herrero, S.; Garcia-López, M. T.; Cennaruzabeitia, E.; Del Rio, J.; Herranz, R. Tetrahedron 2003, 59, 4491. (c) Lindner, A. S.; Geist, E.; Gjikaj, M.; Schmidt, A. J. Heterocycl. Chem. 2014, 51, 423. (d) Murugesan, N.; Gu, Z.; Lee, V.; Webb, M. L.; Liu, E. C. K.; Hermsmeier, M.; Hunt, J. T. Bioorg. Med. Chem. Lett. 1995, 5, 253. (e) Ettari, R.; Pinto, A.; Tamborini, L.; Angelo, I. C.; Grasso, S.; Zappalà, M.; Capodicasa, N.; Yzeiraj, L.; Gruber, E.; Aminake, M. N.; Pradel, G.; Schirmeister, T.; De Micheli, C.; Conti, P. Chem. Med. Chem. 2014 , 9, 1817.

  7. Blass, B. E.; Burt, T. M.; Liu, S.; Portlock, D. E.; Swing, E. M. Tetrahedron Lett. 2000, 41, 2063.

    Article  CAS  Google Scholar 

  8. Zats, G. M.; Kovaliov, M.; Albeck, A.; Shatzmiller, Sh. J. Pept. Sci. 2015, 21, 512.

    Article  CAS  Google Scholar 

  9. (a) Rakib, E. M.; Benchidmi, M.; Essassi, E. M.; El Bouadili, A.; Ibn Mansour, A.; Bellan, J.; Lopez, L.; Lamandé, L. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2000, 39B, 339. (b) Bogdal, D. Molecules 1999, 4, 333.

  10. (a) Karp, G. M.; Manfredi, M. C.; Guaciaro, M. A.; Ortlip, Ch. L.; Marc, P.; Szamosi, I. T. J. Agric. Food. Chem. 1997, 45, 493. (b) Singh, B. K.; Szamosi, I. T.; Dahlke, B. J.; Karp, G. M.; Shaner, D. L. Pestic. Biochem. Physiol. 1996, 56, 62. (c) Guaciaro, M. A.; Harrington, P. M.; Karp, G. M. US Patent 5438035.

  11. Chkanikov, D. I.; Sokolov, M. S. Herbicidal Effects of 2,4-D and Other Halogenated Phenoxy Acids [in Russian]; Nauka: Moscow, 1973, p. 215.

  12. (a) Pitina, M. R.; Poznanskaya, N. L.; Promonenkov, V. K.; Shvetsov-Shilovskiy, N. I. Agrokhimiya 1986, 4, 107. (b) Spiridonov, Yu. Ya.; Khokhlov, P. S.; Shestakov, V. G. Agrokhimiya 2009, 5, 81.

  13. Dmitrieva, I. G.; Dyadyuchenko, L. V.; Strelkov, V. D.; Isakova, L. I.; Krapivin, G. D.; Zaplishnyi, V. N. RU Patent 2276845; Byul. Izobret. 2006, (15).

  14. (a) Strelkov, V. D.; Dyadyuchenko, L. V.; Isakova, L. I.; Kvasenkov, O. I. RU Patent 2277333; Byul. Izobret. 2006, (16). (b) Dmitrieva, I. G.; Dyadyuchenko, L. V.; Strelkov, V. D.; Isakova, L. I.; Tkach, L. N.; Nazarenko, D. Yu.; Chubenko, T. I.;Tymorin, V. A.; Nen'ko, N. I.; Krapivin, G. D.; Dyadyuchenko, L. V.; Isakova, L. I.; Strelkov, V. D. RU Patent 2232762; Byul. Izobret. 2004, (20).

  15. Strelkov, V. D.; Dyadyuchenko, L. V.; Isakova, L. I.; Dmitrieva, I. G. Agrokhimiya 2010, 28.

Download references

This work was carried out within the framework of the Federal targeted program " Research and Development in the Priority Areas of Development of the Russian Scientific and Technological Complex for years 2014–2020". The identification code of applied scientific research (project) is RFMEF157714X0046.

Author information

Authors and Affiliations

  1. Kuban State Technological University, 2 Moskovskaya St, Krasnodar, 350072, Russia

    Tat’yana A. Stroganova, Vladimir K. Vasilin & Gennady D. Krapivin

  2. Kuban State University, 149 Stavropol’skaya St, Krasnodar, 350040, Russia

    Vladimir D. Strelkov

  3. All-Russian Scientific Research Institute of Biological Plant Protection, Russian Academy of Agricultural Sciences, PO Box 5269, Krasnodar, 350039, Russia

    Ludmila V. Dyadyuchenko

Authors
  1. Tat’yana A. Stroganova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vladimir K. Vasilin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gennady D. Krapivin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Vladimir D. Strelkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ludmila V. Dyadyuchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vladimir K. Vasilin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(1), 45–51

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Stroganova, T.A., Vasilin, V.K., Krapivin, G.D. et al. Synthesis of N-alkylated benzo- and pyridothienopyrrolo-[1,2a][1,4]diazepin-6-ones acting as antidotes against the herbicide 2,4-D. Chem Heterocycl Comp 52, 45–51 (2016). https://doi.org/10.1007/s10593-016-1830-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1830-x

Keywords

Search

Navigation