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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1748–1756 | Cite as

Studies of Imidazo[1,2-a]Benzimidazoles 32*. Synthesis and Properties of 2,3-Dihydroimidazo-and 2,3,4,10-Tetrahydropyrimido[1,2-a]Benzimidazol-9(10)-Ylacetic Acids

  • V. A. AnisimovaEmail author
  • I. E. Tolpygin
  • O. I. Askalepova
Article

Reaction of unsubstituted 2,9-dihydro-3H-imidazo- and 2,3,4,10-tetrahydropyrimido[1,2-a]benz-imidazoles with haloacetates has given hetaryl-9(10)-acetates. The basic and acid hydrolysis of these esters yields the corresponding acids. The zwitterionic structure of the acids obtained has been proved. They were also prepared by the direct alkylation of unsubstituted azaheterocycles using sodium chloroacetate or by hydrolysis of the corresponding acetonitriles. The synthesized esters readily undergo aminolysis and hydrazinolysis.

Keywords

amides betaines 2,9-dihydro-3H-imidazo[1,2-a]benzimidazoles hetarylacetic acids hydrazides 2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles basicity protolytic equilibrium 

References

  1. 1.
    V. A. Anisimova, I. E. Tolpygin, and G. S. Borodkin, Khim. Geterotsikl. Soedin., 1379 (2013). [Chem. Heterocycl. Compd., 49, 1285 (2013)].Google Scholar
  2. 2.
    V. A. Anisimova, I. E. Tolpygin, A. A. Spasov, V. A. Kosolapov, M. P. Samokhina, A. V. Stepanov, and A. A. Orlova, Khim.-Farm. Zh., 41, No. 3, 9 (2007). [Pharm. Chem. J., 41, No. 3, 126 (2007)].Google Scholar
  3. 3.
    V. A. Anisimova, A. A. Spasov, I. E. Tolpygin, M. V. Chernikov, D. S. Yakovlev, I. I. Goryagin, N. A. Gurova, O. A. Salaznikova, L. V. Naumenko, V. A. Kosolapov, L. V. El’tsova, and N. A. Kolobrodova, Khim.-Farm. Zh., 44, No. 5, 8 (2010). [Pharm. Chem. J., 44, No. 5, 241 (2010)].Google Scholar
  4. 4.
    V. A. Anisimova, I. E. Tolpygin, A. A. Spasov, D. S. Yakovlev, N. A. Kolobrodova, N. A. Gurova, O. A. Salaznikova, L. V. Naumenko, V. A. Kosolapov, L. V. El’tsova, T. M. Mitina, M. P. Voronkova, and K. V. Lenskaya, Khim.-Farm. Zh., 44, No. 6, 3 (2012). [Pharm. Chem. J., 46, No. 6, 325 (2012)].Google Scholar
  5. 5.
    V. A. Anisimova, M. M. Osipova, T. A. Kuzmenko, D.-H. Caignard, P. Renard, and D. Manechez, FR Pat. Appl. 2765223.Google Scholar
  6. 6.
    B. Pirotte, G. Dive, J. Delarge, B. Maseree, L. Dupont, L. Thunus, M. Schynts, J. Coyette, and J. M. Frere, Eur. J. Med. Chem., 27, 193 (1992).CrossRefGoogle Scholar
  7. 7.
    K. Ogawva, I. Yamawaki, Y. I. Matsusita, N. Nomura, P. F. Kador, and J. H. Kinoshita, Eur. J. Med. Chem., 28, 769 (1993).CrossRefGoogle Scholar
  8. 8.
    S. K. Singh, N. Manne, P. C. Ray, and M. Pal, Beilstein J. Org. Chem., 4, No. 42, 4 (2008).Google Scholar
  9. 9.
    R. J. Herr, Bioorg. Med. Chem., 10, 3379 (2002).CrossRefGoogle Scholar
  10. 10.
    V. A. Anisimova, A. A. Spasov. V. A. Kosolapov, I. E. Tolpygin, E. V. Tibir'kova, O. A. Salaznikova, V. A. Kuznetsova, N. A. Gurova, K. V. Lenskaya, D. S. Yakovlev, D. V. Mal’tsev, N. A. Kolobrodova, T. M. Mitina, and O. Yu. Grechko, Khim.-Farm. Zh., 46, No. 11, 15 (2012). [Pharm. Chem. J., 46, No. 11, 647 (2013)].Google Scholar
  11. 11.
    V. Colotta, L. Cecchi, D. Catarzi, G. Filacchioni, A. Galli, and F. Mori, Eur. J. Med. Chem., 29, 95 (1994).CrossRefGoogle Scholar
  12. 12.
    E. Lukevics, S. Germane, I. Segal, and A. Zablotskaya, Khim. Geterotsikl. Soedin., 270 (1997). [Chem. Heterocycl. Comp., 33, 234 (1997)].Google Scholar
  13. 13.
    S. D. Larsen, M. A. Connell, M. M. Cudahy, B. R. Evans, P. D. May, M. D. Meglasson, T. J. O’Sullivan, H. J. Schostarez, J. C. Sih, F. C. Stevens, S. P. Tanis, C. M. Tegley, J. A. Tucker, V. A. Vaillancourt, T. J. Vidmar, W. Watt, and J. H. Yu, J. Med. Chem., 44, 1217 (2001).CrossRefGoogle Scholar
  14. 14.
    A. T. Balaban, D. C. Oniciu, and A. R. Katritzky, Chem. Rev., 104, 2777 (2004).CrossRefGoogle Scholar
  15. 15.
    S. Gao, Z.-Y. Zhang, L.-H. Huo, J.-G. Zhao, S. M. Zain, and S. W. Ng, Acta Crystallogr., Sect. E: Struct. Rep. Online, 60, o1006 (2004).Google Scholar
  16. 16.
    P. Haake, L. P. Bausher, and J. P. McNeal, J. Am. Chem. Soc., 93, 7045 (1971).CrossRefGoogle Scholar
  17. 17.
    A. Ljungqvist and K. Folkers, Acta Chem. Scand., Ser. B, 42, 408 (1988).CrossRefGoogle Scholar
  18. 18.
    T. Saegusa and S. Kobayashi, Pure. Appl. Chem., 50, 281 (1978).CrossRefGoogle Scholar
  19. 19.
    R. J. North and A. R. Day, J. Heterocycl. Chem., 6, 655 (1969).CrossRefGoogle Scholar
  20. 20.
    A. R. Katritzky, G. L. Sommen, A. V. Gromova, R. M. Witek, P. J. Steel, and R. Damavarapu, Khim. Geterotsikl. Soedin., 127 (2005). [Chem. Heterocycl. Compd., 41, 111 (2005)].Google Scholar
  21. 21.
    G. A. Gol’dfarm and L. S. Kondakova, Zh. Obshch. Khim., 10, 1055 (1940).Google Scholar
  22. 22.
    I. Ya. Bershtein and Yu. L. Kaminsky, Spectrophotometric Analysis in Organic Chemistry [In Russian], Khimiya, Leningrad (1986), p. 115-150.Google Scholar
  23. 23.
    J. Incedy, Using Complexes in Analytical Chemistry [Russian translation], Mir, Moscow (1979), pp. 26-31, 76-84.Google Scholar
  24. 24.
    S. Guha, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., B29, 2163 (1973).Google Scholar
  25. 25.
    T. Mas, R. M. Claramunt, M. D. Santa Maria, D. Sanz, S. H. Alarcon, M. Perez-Torralba, and J. Elguero, ARKIVOC, v, 48 (2002).Google Scholar
  26. 26.
    A. E. Kuusk, Zh. Org. Khim., 19, 485 (1983).Google Scholar
  27. 27.
    V. A. Anisimova, M. V. Levchenko, Yu. V. Koshchienko, and A. F. Pozharskii, USSR Inventor's Certificate 952847; Byul Izobr., No. 31, 126 (1982).Google Scholar
  28. 28.
    V. A. Anisimova, M. V. Levchenko, T. V. Korochina, A. A. Spasov, S. G. Kovalev, and G. P. Dudchenko, US Pat. Appl. 5623073.Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • V. A. Anisimova
    • 1
    Email author
  • I. E. Tolpygin
    • 1
  • O. I. Askalepova
    • 2
  1. 1.Scientific-Research Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-the-DonRussia
  2. 2.Chemistry FacultySouthern Federal UniversityRostov-on-the-DonRussia

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