Skip to main content
SpringerLink
Log in

Cyclocondensation of n-(prop-2-yn-1-yl)- and n-(penta-2,4-diyn-1-yl)- o-phenylenediamines with phenyl isothiocyanate and carbon disulfide

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The cyclocondensation of N-(prop-2-yn-1-yl)-o-phenylenediamines with phenyl isothiocyanate leads to the formation of 1-(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazole-2-thiones irrespective of the substituent nature at the triple bond. Reactions of both mono- and diacetylenic derivatives of o-phenylenediamine with carbon disulfide in the presence of KOH proceed with the formation of two heterocyclic nuclei simultaneously. From N-(prop-2-yn-1-yl)-o-phenylenediamines containing an aryl substituent at the triple bond, and N-(penta-2,4-diyn-1-yl)-o-phenylenediamines 2-methylidene-2,3-dihydro[1,3]thiazolo[3,2-a]benzimidazoles are formed. The latter are readily isomerized under the action of base giving thiazolo[3,2-a]benzimidazoles. The cyclocondensation of N-(alk-2-yn-1-yl)-o-phenylenediamines with CS2 leads to [1,3]thiazino[3,2-a]benzimidazoles.

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

Similar content being viewed by others

References

  1. R. Crossley, US Pat. 4873237 (1989); Chem. Abstr., 112, 198401 (1990).

    Google Scholar 

  2. N. H. Grant and D. E. Clark, US Pat. 4361574 (1982); Chem. Abstr., 98, 101200 (1983).

    Google Scholar 

  3. C. M. Rogers, T. J. Rogers, and S. C. Gilman, J. Immunopharmacol., 7, 479 (1985).

    Article  CAS  Google Scholar 

  4. R. I. Fenichel, F. J. Gregory, and H. E. Alburn, Br. J. Cancer, 33, 329 (1976).

    Article  CAS  Google Scholar 

  5. H. A. Abdel-Aziz, A. M. Gamal-Eldeen, N. A. Hamdy, and I. M. I. Fakhr, Arch. Pharm., 342, 230 (2009).

    Article  CAS  Google Scholar 

  6. V. M. Dianov, Khim.-farm. Zh., 41, No. 6, 20 (2007).

    Google Scholar 

  7. J. J. D’Amico, R. H. Campbell, and E. C. Guinn, J. Org. Chem., 29, 865 (1964).

    Article  Google Scholar 

  8. A. E. Alper and A. Taurins, Can. J. Chem., 45, 2903 (1967).

    Article  CAS  Google Scholar 

  9. A. N. Krasovskii and P. M. Kochergin, Khim. Geterotsikl. Soedin., 899 (1967). [Chem. Heterocycl. Comp., 3, 709 (1967)].

    Article  Google Scholar 

  10. A. N. Krasovskii, P. M. Kochergin, and L. V. Samoilenko, Khim. Geterotsikl. Soedin., 827 (1970). [Chem. Heterocycl. Comp., 6, 766 (1970)].

    Article  Google Scholar 

  11. A. A. O. Sarhan, H. A. H. El-Sherief, and A. M. Mahmoud, Tetrahedron, 52, 10485 (1966).

    Article  Google Scholar 

  12. K. K. Balasubramanian and B. Venugopalan, Tetrahedron Lett., 15, 2643 (1974).

    Article  Google Scholar 

  13. K. K. Balasubramanian and B. Venugopalan, Tetrahedron Lett., 15, 2645 (1974).

    Article  Google Scholar 

  14. M. M. Heravi, A. Keivanloo, M. Rahimizadeh, M. Bakavoli, and M. Ghassemzadeh, Tetrahedron Lett., 45, 5747 (2004).

    Article  CAS  Google Scholar 

  15. A. N. Krasovskii and P. M. Kochergin, Khim.-farm. Zh., 2, No. 10, 18 (1968).

    CAS  Google Scholar 

  16. A. A. Shklyarenko, V. V. Yakovlev, and V. N. Chistokletov, Zh. Org. Khim., 40, 617 (2004).

    Google Scholar 

  17. K. Ikeda, S.-I. Hata, Y. Tanaka, and T. Yamamoto, Org. Prep. Proc. Int., 32, 401 (2000).

    Article  CAS  Google Scholar 

  18. R. V. Novikov, M. E. Borovitov, and I. A. Balova, Khim. Geterotsikl. Soedin., 627 (2008). [Chem. Heterocycl. Comp., 44, 494 (2008)].

    Article  CAS  Google Scholar 

  19. N. Yu. Sipkina and I. A. Balova, Zh. Obshch. Khim., 73, 2002 (2003).

    Google Scholar 

  20. U. Vögeli, W. von Philipsborn, K. Nagarajan, and M. D. Nair, Helv. Chem. Acta, 61, 607 (1978).

    Article  Google Scholar 

  21. P. Sohar, Z. Szöke-Molnar, G. Stajer, and G. Bernath, Magn. Reson. Chem., 27, 959 (1989).

    Article  CAS  Google Scholar 

  22. Y. Kurasawa, R. Katoh, A. Takada, H. S. Kim, and Y. Okamoto, J. Heterocycl. Chem., 29, 1001 (1992).

    Article  CAS  Google Scholar 

  23. V. S. Berseneva, A. V. Tkachev, Yu. Yu. Morzherin, W. Dehaen, I. Luyten, S. Toppet, and V. A. Bakulev, J. Chem. Soc., Perkin Trans. 1, 2133 (1998).

  24. G. Stájer, A. E. Szabó, and P. Sohár, Heterocycles, 51, 1849 (1999).

    Article  Google Scholar 

  25. V. S. Berseneva, Yu. Yu. Morzherin, W. Dehaen, I. Luyten, and V. A. Bakulev, Tetrahedron, 57, 2179 (2001).

    Article  CAS  Google Scholar 

  26. V. A. Bakulev, V. S. Berseneva, N. P. Belskaia, Yu. Yu. Morzherin, A. Zaitsev, W. Dehaen, I. Luyten, and S. Toppet, Org. Biomol. Chem., 1, 134 (2003).

    Article  CAS  Google Scholar 

  27. U. Vögeli and W. von Philipsborn, Org. Magn. Reson., 7, 617 (1975).

    Article  Google Scholar 

  28. U. Vögeli, D. Herz, and W. von Philipsborn, Org. Magn, Reson. 13, 200 (1980).

    Article  Google Scholar 

  29. L. Brandsma and H. D. Verkruijsse, Synthesis of Acetylenes, Allenes, and Cumulenes. A Laboratory Manual, Elsevier (1981), p. 221.

    Google Scholar 

Download references

The authors are deeply grateful to associate professor S. I. Selivanova for recording the NMR spectra. The authors thank the Saint-Petersburg State University for financial support (Research grant 12.38.14.2011).

Author information

Authors and Affiliations

  1. Saint-Petersburg State University, 26 Universitetskiy Pr., Saint Petersburg, 198504, Russia

    R. V. Novikov, N. A. Danilkina & I. A. Balova

Authors
  1. R. V. Novikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. A. Danilkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. A. Balova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. A. Balova.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 917–927, June, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Novikov, R.V., Danilkina, N.A. & Balova, I.A. Cyclocondensation of n-(prop-2-yn-1-yl)- and n-(penta-2,4-diyn-1-yl)- o-phenylenediamines with phenyl isothiocyanate and carbon disulfide. Chem Heterocycl Comp 47, 758–766 (2011). https://doi.org/10.1007/s10593-011-0831-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0831-z

Keywords

Search

Navigation