Skip to main content
SpringerLink
Log in

Unexpected transformation of 1,5-benzodiazepine derivatives under imidazo-annulation reaction conditions

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

In an attempt to synthesize new derivatives of imidazo[1,5-a][1,5]benzodiazepine-3-carboxylic acid esters by activation of the amide group of the heterocycle to iminophosphate and its cyclocondensation with ethyl isocyanoacetate, unexpected 5-substituted ethyl oxazole-4-carboxylates were obtained as the main products. Structures of the novel oxazole derivatives were confirmed by IR, 1H, 13C, and 31P NMR, and mass spectra, and the reaction course was rationalized using computational molecular modeling techniques.

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

Figure 1
Figure 2

Similar content being viewed by others

References

  1. (a) Page, C.; Michael, C.; Sutter, M.; Walker, M.; Hoffman, B. Intergrated Pharmacology; Mosby: London, 2005, 2nd ed. (b) Grossi, G.; Di Braccio, M.; Roma, G.; Ballabeni, V.; Barocelli, E. Eur. J. Med. Chem. 2002, 37, 933. (c) Farhid, H.; Khodkari, V.; Nazeri, M. T.; Javanbakht, S.; Shaabani, A. Org. Biomol. Chem. 2021, 19, 3318. (d) Caiana, E. C.; de Veras, B. O.; de Souza, A. L.; Queiroz, N. J. Braz. Chem. Soc. 2021, 32, 626.

  2. (a) Ananthan, S.; Clayton, S. D.; Ealick, S. E.; Wong, G.; Evoniuk, G. E.; Skolnick, P. J. Med. Chem. 1993, 36, 479. (b) Walser, A.; Flynn, T.; Fryer, R. I. J. Heterocycl. Chem. 1978, 15, 577. (c) Fryer, R. I.; Pinto, J. C.; Upasani, R. B. J. Heterocycl. Chem. 1993, 30, 945.

  3. (a) Anzini, M.; Braile, C.; Valenti, S.; Cappelli, A.; Vomero, S.; Marinelli, L.; Limongelli, V.; Novellino, E.; Betti, L.; Giannaccini, G.; Lucacchini, A.; Ghelardini, C.; Norcini, M.; Makovec, F.; Giorgi, G.; Fryer, R. I. J. Med. Chem. 2008, 51, 4730. (b) Auta, J.; Kadriu, B.; Giusti, P.; Costa, E.; Guidottti, A. Pharmacol. Biochem. Behav. 2010, 95, 383.

  4. Revot, T. D.; Li, G.; Cook, J. M.; Sibille, E. ACS Chem. Neurosci. 2019, 10, 2088.

    Article  Google Scholar 

  5. (a) Li, X.; Yu, J.; Atack, J. R.; Cook, J. M. Med. Chem. Res. 2004, 13, 259. (b) Xu, N. Z.; Ernst, M.; Treven, M.; Cerne, R.; Wakulchik, M.; Li, X.; Jones, T. M.; Gleason, S. D.; Morrow, D.; Schkeryantz, J. M.; Rahman, M. T.; Li, G.; Poe, M. M.; Cook, J. M.; Witkin, J. M. Psychopharmacology 2018, 235, 1151.

  6. Li, G.; Stephen, M. R.; Kodali, R.; Zahn, N. M.; Poe, M. M.; Tiruveedhula, V. V. N. P. B.; Huber, A. T.; Schussman, M. K.; Qualmann, K.; Panhans, C. M.; Raddatz, N. J.; Baker, D. A.; Prevot, T. D.; Banasr, M.; Sibille, E.; Arnold, L. A.; Cook, J. M. ARKIVOC 2018, (iv), 158.

  7. (a) Watjen, F.; Baker, R.; Engelstoff, M.; Herbert, R.; MacLeod, A.; Knight, A.; Merchant, K.; Moseley, J.; Saunders, J.; Swain, C. J.; Wong, E.; Springer, J. P. J. Med. Chem. 1989, 32, 2282. (b) Hoffman, E. J.; Waren, E. W. Clin. Pharm. 1993, 12, 699.

  8. Whitwam, J. G.; Amrein, R. Acta Anaesthesiol. Scand., Suppl. 1995, 108, 3.

  9. (a) Puodziunaite, B. D.; Janciene, R.; Kosychova, L.; Stumbreviciute, Z. ARKIVOC 2000, (iv), 512. (b) Kosychova, L.; Pleckaitiene, L.; Staniulyte, Z.; Janciene, R.; Palaima, A.; Puodziunaite, B. ARKIVOC 2006, (xiii), 158.

  10. (a) Weber, M.; Bartsch, H.; Erker, T. Monatsh. Chem. 2002, 133, 653. (b) Bromidge, S. M.; Arban, R.; Bertani, B.; Bison, S.; Borriello, M.; Cavanni, P.; Dal Forno, G.; Di-Fabio, R.; Donati, D.; Fontana, S.; Gianotti, M.; Gordon, L. J.; Granci, E.; Leslie, C. P.; Moccia, L.; Pasquarello, A.; Sartori, I.; Sava, A.; Watson, J. M.; Worby, A.; Zonzini, L.; Zucchelli, V. J. Med. Chem. 2010, 53, 5827.

  11. (a) Hesse, M.; Meier, H.; Zeeh, B. Spektroskopische Methoden in der Organischen Chemie; Thieme: Stuttgart, 1984, p. 453. (b) Buchanan, G. W.; Beneza C. Can. J. Chem. 1976, 54, 231. (c) Das, D.; Brahmmananda Rao, C. V. S.; Sivaraman, N.; Sivaramakrishna, A.; Vijayakrishna, K. Inorg. Chim. Acta 2018, 482, 597.

  12. (a) Puodziunaite, B. D.; Vertelyte, L.; Janciene, R.; Stumbreviciute, Z. OPPI 1997, 29, 689. (b) Puodziunaite, B. D.; Kosychova, L.; Janciene, R.; Stumbreviciute, Z. Monatsh. Chem. 1997, 128, 1275.

  13. (a) Kalinovski, H.-O.; Berger, S.; Braun, S. 13C-NMRSpektroskopie; Thieme: Stutgart, 1984, p. 686. (b) Data, S.; Wai, J. L.; Kumar, S.; Cameron, A. J.; Trehet, M.; Itumoh, E. J.; Feld, J.; Söhnel, T.; Leitao, E. M. Eur. J. Org. Chem. 2021, 40, 5468. (c) Elguero, J.; Fruchier, A.; Jimeno, M. L.; Molina, P. J. Chem. Res., Synop. 2002, 34. (d) Perez-Prieto, J.; Galian, R. E.; Miranda, M. A.; Catalina, F.; Martin-Vargas, N.; Lopez-Ortiz, F. Org. Lett. 2004, 6, 561.

  14. (a) Janciene, R.; Vektariene, A.; Stumbreviciute, Z.; Kosychova, L.; Konstantinavicius, K.; Puodziunaite, B. D. Monatsh. Chem. 2003, 134, 1629. (b) Janciene, R.; Vektariene, A.; Stumbreviciute, Z.; Puodziunaite, B. D. Monatsh. Chem. 2011, 142, 609. (c) Vektariene, A.; Vektaris, G. Heteroat. Chem. 2004, 15, 263. (d) Vektarienė, A. Lith. J. Phys. 2018, 58, 232.

  15. (a) Pearson, R. G. J. Chem. Educ. 1968, 45, 643. (b) Pearson, R. G. Science 1966, 151, 172.

  16. Klopman, G. J. Am. Chem. Soc. 1968, 90, 223.

    Article  CAS  Google Scholar 

  17. Kornblum, N.; Smiley, R. A.; Blackwood, R. K.; Iffland, D. C. J. Am. Chem. Soc. 1955, 77, 6269.

    Article  CAS  Google Scholar 

  18. (a) Wang, X.; Li, Z.; Zhu, X.; Mao, H.; Zou, X.; Kong, L.; Li, X. Tetrahedron 2008, 64, 6510. (b) Ried, W.; Stahlhofen, P. Chem. Ber. 1957, 90, 828.

Download references

Computations were performed on resources of the supercomputer ''VU HPC'' at the Vilnius University, Faculty of Physics.

Author information

Authors and Affiliations

  1. Vilnius University, Life Sciences Centre, Institute of Biochemistry, 12A Mokslininkų St, LT-08412, Vilnius, Lithuania

    Mantas Jonušis, Gema Mikulskienė, Simona Jonušienė & Regina Jančienė

  2. Vilnius University, Institute of Theoretical Physics and Astronomy, 3 Saulėtekio St, LT-10257, Vilnius, Lithuania

    Aušra Vektarienė

  3. Vilnius University, Life Sciences Centre, 7 Saulėtekio St, LT-10257, Vilnius, Lithuania

    Dalia Vektarytė

Authors
  1. Mantas Jonušis
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Aušra Vektarienė
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gema Mikulskienė
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Simona Jonušienė
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Dalia Vektarytė
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Regina Jančienė
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mantas Jonušis.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(4/5), 283–288

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 872 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jonušis, M., Vektarienė, A., Mikulskienė, G. et al. Unexpected transformation of 1,5-benzodiazepine derivatives under imidazo-annulation reaction conditions. Chem Heterocycl Comp 59, 277–282 (2023). https://doi.org/10.1007/s10593-023-03194-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-023-03194-y

Keywords

Search

Navigation