Skip to main content
SpringerLink
Log in

A novel method for the synthesis of pyrimido[1,2-a]benzimidazoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Condensation of 1,2-diaminobenzimidazole with N-arylitaconimides was studied. It was found that 2-(10-amino-N-aryl-2-oxo-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazol-3-yl)acetamides were formed in the course of this reaction upon brief heating to reflux of the reagent mixture in 2-propanol in the presence of catalytic amounts of acetic acid.

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

Fig. 1
Figure 2

Similar content being viewed by others

References

  1. (a) Gala, D.; DiBenedetto, D. J.; Kugelman, M.; Mitchell, M. B. Tetrahedron Lett. 2003, 44, 2721. (b) Abdel-Mohsen, H. T.; Regab, F. A. F.; Ramla, M. M.; El Diwani, H. I. Eur. J. Med. Chem. 2010, 45, 2336. (c) Chandra; Puttaraju, K. B.; Mahesh, S. S.; Shivashankar, K.; Lokanath, N. K.; Madegowda, M. J. Biomed. Inform. 2014, 10, 288. (d) Rupert, K. C.; Henry, J. R.; Dodd, J. H.; Wadsworth, S. A.; Cavender, D. E.; Olini, G. C.; Fahmy, B.; Siekierka, J. J. Bioorg. Med. Chem. Lett. 2003, 13, 347. (e) Clements-Jewery, S.; Dansawan, G.; Gardener, C. R.; Matharu, S. S.; Murdoch, R.; Tully, W. R.; Westwood, R. J. Med. Chem. 1988, 31, 1220. (f) Meshram, H. M.; Kumar, A. S; Kumar, G. S.; Swetha, A.; Reddy, B. Ch.; Ramesh, P. Pharma Chem. 2012, 4, 956.

  2. (a) Rudenko, R. V.; Komykhov, S. A.; Musatov, V. I.; Konovalova, I. A.; Shishkin, O. V.; Desenko, S. M. J.Heterocycl. Chem. 2011, 48, 888. (b) Shikhaliev, Kh. S.; Potapov, A. Yu.; Kryl'skii, D. V. Russ. Chem. Bull., Int. Ed. 2007, 56, 367. [Izv. Akad. Nauk, Ser. Khim. 2007, 355.] (c) Shikhaliev, Kh. S.; Kryl'skii, D. V.; Potapov, A. Yu.; Krysin, M. Yu.; Trefilova, I. N. Izv. Vuzov Khim. i Khim. Tekhnol. 2004, 47(3), 149. (d) Kovygin, Yu. A.; Shikhaliev, Kh. S.; Potapov, A. Yu.; Kryl'skii, D. V. Izv. Vuzov Khim. i Khim. Tekhnol. 2005, 48(1), 59.

  3. (a) Romano, C.; Cuesta, E.; Avendano, C. Heterocycles 1990, 31 , 267. (b) Vandyshev, D. Yu.; Shikhaliyev, H. S.; Potapov, A. Yu. Eur. Chem. Bull. 2015, 4, 424. (c) Morkovnik, A. S.; Kuz'menko, T. A.; Divaeva, L. N.; Borodkin, G. S. Rus. J. Org. Chem. 2013, 49, 895. [Zh. Org. Khim. 2013, 909.] (d) Klyuev, N. A.; Povstyanoi, M. V.; Orlov, V. M.; Gnidets,. P.; Kruglenko, V. P. Chem. Heterocycl. Compd. 1992, 28, 779. [Khim. Geterotsikl. Soedin. 1992, 937.] (e) Kuz'menko, T. A.; Kuz'menko, V. V.; Pozharskii, A. F.; Simonov, A. M. Chem. Heterocycl. Compd. 1988, 24, 880. [Khim. Geterotsikl. Soedin. 1988, 1070.]

  4. Medway, A. M.; Sperry, J. Green Chem. 2014, 16, 2084.

    Article  CAS  Google Scholar 

  5. (a) Filimonov, S. I.; Korsakov, M. K.; Chirkova, Zh. V.; Abramov, I. G.; Stashina, G. A.; Firgang, S. I.; Kovygin, Yu. A.; Shikhaliev, Kh. S. Chem. Heterocycl. Compd. 2013, 49, 993. [Khim. Geterotsikl. Soedin. 2013, 1065.] (b) Rudenko, R. V.; Komykhov, S. A.; Desenko, S. M.; Musatov, V. I.; Shishkin, O. V.; Konovalova, I. A.; Vashchenko, E. V.; Chebanov, V. A. Synthesis 2011, 783.

  6. (a) Pozharskii, A. F.; Anisimova, V. A.; Tsupak, E. B. Laboratory Experiments in Heterocyclic Chemistry [in Russian]; Rostov University, 1985, p. 106. (b) Oishi, T. Polym. J. 1980, 12, 719. (b) Abdel-Naby, A. S. J. Appl. Polym. Sci. 2011, 121, 169. (c) Hegazy, M.-E. F.; Shishido, K.; Hirata, T. Tetrahedron: Asymmetry 2006, 17, 1859. (d) Leow, D.; Lin, S.; Chittimalla, S. K.; Fu, X.; Tan, C.-H. Angew. Chem., Int. Ed. 2008, 47, 5641. (e) Zhang, X.; Li, Z.-C.; Li, K.-B.; Du, F.-S.; Li, F.-M. J. Am. Chem. Soc. 2004, 126, 12200.

Download references

This work was supported by the Federal targeted program ''Research and Development in the Priority Areas of Development of the Russian Scientific and Technological Complex for years 2014–2020.'' (Agreement № 14.577.21.0182, the unique identifier for applied scientific research RFMEFI57715X0182).

Author information

Authors and Affiliations

  1. Voronezh State University, 1 Universitetskaya Sq., Voronezh, 394006, Russia

    Dmitriy Yu. Vandyshev, Khidmet S. Shikhaliev, Anna V. Kokonova, Andrei Yu. Potapov, Maria G. Kolpakova & Artem L. Sabynin

  2. People’s Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Fedor I. Zubkov

Authors
  1. Dmitriy Yu. Vandyshev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Khidmet S. Shikhaliev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Anna V. Kokonova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Andrei Yu. Potapov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Maria G. Kolpakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Artem L. Sabynin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Fedor I. Zubkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Dmitriy Yu. Vandyshev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(7), 493–497

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 738 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vandyshev, D.Y., Shikhaliev, K.S., Kokonova, A.V. et al. A novel method for the synthesis of pyrimido[1,2-a]benzimidazoles. Chem Heterocycl Comp 52, 493–497 (2016). https://doi.org/10.1007/s10593-016-1914-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1914-7

Keywords

Search

Navigation