Skip to main content
SpringerLink
Log in

4H-Chromenes as 1,3-bielectrophiles in the reaction with 2-aminobenzimidazole: synthesis of pyrimido[1,2-a]benzimidazoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A method for the preparation of pyrimido[1,2-a]benzimidazoles containing a 2-hydroxybenzyl or (2-hydroxynaphthalen-1-yl)methyl group at position 3 was proposed based on the reaction of β-carbonyl-substituted 4H-chromenes and their benzo analogs with 2-aminobenzimidazole. In the case of chromenes substituted in the methylene fragment, 7,13a-dihydro-5H-benzo[5',6']chromeno-[3',2':5,6]pyrimido[1,2-a]benzimidazoles were isolated.

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) Begunov, R. S.; Ryzvanovich, G. A. Russ. Chem. Rev. 2013, 82, 77. [Usp. Khim. 2013, 82, 77.] (b) Goel, R.; Luxami, V.; Paul, K. RSC Adv. 2015, 5, 81608. b Jismy, B.; Akssira, M.; Knez, D.; Guillaumet, G.; Gobec, S.; Abarbri, M. New J. Chem. 2019, 43, 9961. c Fedotov, V. V.; Rusinov, V. L.; Ulomsky, E. N.; Mukhin, E. M.; Gorbunov, E. B.; Chupakhin, O. N. Chem. Heterocycl. Compd. 2021, 57, 383. [Khim. Geterotsikl. Soedin. 2021, 57, 383.]

  2. Asobo, P. F.; Wahe, H.; Mbafor, J. T.; Nkengfack, A. E.; Fomum, Z. T.; Sopbue, E. F.; Döpp, D. J. Chem. Soc., Perkin Trans. 1 2001, 457.

  3. Risley, V. A.; Henry, S.; Kosyrikhina, M. V.; Manzanares, M. R.; Payan, I.; Downer, C. D.; Hellmann, C. C.; Van Slambrouck, S.; Frolova, L. V. Chem. Heterocycl. Compd. 2014, 50, 185. [Khim. Geterotsikl. Soedin. 2014, 209.]

  4. Shaaban, M. R.; Saleh, T. S.; Mayhoub, A. S.; Mansour, A.; Farag, A. M. Bioorg. Med. Chem. 2008, 16, 6344.

    Article  CAS  Google Scholar 

  5. El-Shorbagi, A.-N. A.; Hussein, M. A. Pharma Chem. 2015, 7(4), 190.

    CAS  Google Scholar 

  6. Zhang, Z.-T.; Qiu, L.; Xue, D.; Wu, J.; Xu, F.-F. J. Comb. Chem. 2010, 12, 225.

    Article  Google Scholar 

  7. Rawat, M.; Rawat, D. S. Tetrahedron Lett. 2018, 59, 2341.

    Article  CAS  Google Scholar 

  8. Zanatta, N.; Amaral, S. S.; Esteves-Souza, A.; Echevarria, A.; Brondani, P. B.; Flores, D. C.; Bonacorso, H. G.; Flores, A. F. C.; Martins, M. A. P. Synthesis 2006, 2305.

  9. Kreutzberger, A.; Leger, M. Arch. Pharm. (Weinheim, Ger.) 1982, 315, 438.

  10. (a) Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Pipko, S. E.; Tolmachev, A. A. Heterocycles 2008, 75, 583. (b) Badran, A.-S.; El-Gohary, N. M.; Ibrahim, M. A.; Hashiem, S. H. J. Heterocycl. Chem. 2020, 57, 2570.

  11. (a) Kreutzberger, A.; Leger, M. J. Heterocycl. Chem. 1981, 18, 1587. (b) Saijo, R.; Watanabe, G.; Kurihara, K.; Kawase, M. Heterocycles 2014, 89, 2334.

  12. Bouillon, J.-P.; Janousek, Z.; Viehe, H. G.; Tinant, B.; Declercq, J.-P. J. Chem. Soc., Perkin Trans. 1 1995, 2907.

  13. Krasovsky, A. L.; Hartulyari, A. S.; Nenajdenko, V. G.; Balenkova, E. S. Synthesis 2002, 133.

  14. Kawase, M.; Hirabayashi, M.; Saito, S.; Yamamoto, K. Tetrahedron Lett. 1999, 40, 2541.

    Article  CAS  Google Scholar 

  15. (a) Belyaev, D. V.; Chizhov, D. L.; Kodess, M. I.; Ezhikova, M. A.; Rusinov, G. L.; Charushin, V. N. Mendeleev Commun. 2019, 29, 249. (b) Goryaeva, M. V.; Burgart, Ya. V.; Saloutin, V. I.; Chupakhin, O. N. Chem. Heterocycl. Compd. 2012, 48, 372. [Khim. Geterotsikl. Soedin. 2012, 395.] (с) Goryaeva, M. V.; Burgart, Ya, V.; Saloutin, V. I. Russ. J. Org. Chem. 2010, 46, 432. [Zh. Org. Khim. 2010, 46, 437.]

  16. Tseng, S.-S.; Epstein, J. W.; Brabander, H. J.; Francisco, G. J. Heterocycl. Chem. 1987, 24, 837.

    Article  CAS  Google Scholar 

  17. Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Targets Heterocycl. Syst. 2018, 22, 436.

    CAS  Google Scholar 

  18. (a) Lukashenko, A. V.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. J. Org. Chem. 2017, 82, 1517. (b) Lukashenko, A. V.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2016, 52, 711. [Khim. Geterotsikl. Soedin. 2016, 52, 711.]

  19. Shakibaei, G. I.; Mirzaei, P.; Bazgir, A. Appl. Catal., A 2007, 325, 188.

  20. CrysAlisPro, version 1.171.38.41; Rigaku Oxford Diffraction, 2015. https://www.rigaku.com/en/products/smc/crysalis.

  21. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.

  22. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

  23. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

Download references

This work was financially supported by the Russian Foundation for Basic Research (contract No. 18-33- 20249).

Author information

Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeyskaya St, Samara, 443100, Russia

    Vitaly А. Osyanin, Dmitry V. Osipov, Kirill S. Korzhenko & Yuri N. Klimochkin

  2. North Caucasus Federal University, 1a Pushkina St, Stavropol, 355009, Russia

    Oleg P. Demidov

Authors
  1. Vitaly А. Osyanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dmitry V. Osipov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kirill S. Korzhenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Oleg P. Demidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yuri N. Klimochkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vitaly А. Osyanin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(5), 588–593

Supplementary Information

ESM 1

(PDF 449 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Osyanin, V.А., Osipov, D.V., Korzhenko, K.S. et al. 4H-Chromenes as 1,3-bielectrophiles in the reaction with 2-aminobenzimidazole: synthesis of pyrimido[1,2-a]benzimidazoles. Chem Heterocycl Comp 57, 588–593 (2021). https://doi.org/10.1007/s10593-021-02947-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-021-02947-x

Keywords

Search

Navigation