Advertisement

Chemistry of Heterocyclic Compounds

, Volume 50, Issue 1, pp 111–116 | Cite as

Synthesis and Recylization of 2,3,9,10-Tetrahydro-8H-[1,4]Dioxino[2,3-f]-[1,3]Thiazino[3,2-a]Benzimidazolium Salts

  • M. A. Orlov
  • I. V. Kapitanov
  • N. I. Korotkikh
  • O. P. Shvaika
Article

A series of [1,3]thiazino[3,2-a]benzimidazolium salts modified in the benzene ring by a condensed 1,4-dioxane ring has been prepared. Reaction with epichlorohydrin occurs with recyclization to form derivatives of 3-(2,3-epithiopropyl)benzimidazol-2-one.

Keywords

3-(2,3-epi-thiopropyl)-1,3,6,7-tetrahydro-2H-[1,4]dioxino[2,3-f]benzimidazol-2-ones 2,3,9,10-tetrahydro-8H-[1,4]dioxino[2,3-f][1,3]thiazino[3,2-a]benzimidazolium salts thiiranes recyclization 

References

  1. 1.
    M. A. Orlov, A. F. Aslanov, and N. I. Korotkikh, Khim. Geterotsikl. Soedin., 440 (2010). [Chem. Heterocycl. Compd., 46, 347 (2010)].Google Scholar
  2. 2.
    N. I. Korotkikh, G. A. Losev, and O. P. Shvaika, in: V. G. Kartsev and G. A. Tolstikov (editors), Nitrogen-containing Heterocycles and Alkaloids [in Russian], Vol. 1, Iridium Press, Moscow (2001), p. 350.Google Scholar
  3. 3.
    A. K. Bagrii, G. F. Galenko, and P. M. Kochergin, Dopovidi Akad. Nauk URSR, Series B, 801 (1975); Chem. Abstr., 84, 43959w (1976).Google Scholar
  4. 4.
    K. Hideg, O. Hankovszky, E. Palosi, G. Hajos, and L. Szporny, US Pat. Appl. 3932395.Google Scholar
  5. 5.
    P. M. Kochergin, A. K. Bagrii, D. V. Kovpak, and G. F. Galenko, USSR Inventor’s Certificate 390094; Ref. Zh. Khim., 17, N464P (1974).Google Scholar
  6. 6.
    A. B. Brukshtus, V. N. Garalene, R.-R. Sirvidite, and V. K. Daukshas, Khim.-Farm. Zh., 26, No. 11-12, 50 (1992).Google Scholar
  7. 7.
    V. Garaliene, L. Labanauskas, and A. Brukštus, Arzneim. Forsch., 56, 282 (2006).Google Scholar
  8. 8.
    B. Das, V. Saidi Reddy, and M. Krishnaiah, Tetrahedron Lett., 47, 8471 (2006).CrossRefGoogle Scholar
  9. 9.
    A. Bellomo and D. Gonzalez, Tetrahedron Lett., 48, 3047 (2007).CrossRefGoogle Scholar
  10. 10.
    E. Lukowska and J. Plenkiewicz, Tetrahedron: Asymmetry, 18, 493 (2007).CrossRefGoogle Scholar
  11. 11.
    A. A. Tomashevskii, V. V. Sokolov, and A. A. Potekhin, Zh. Org. Khim., 1812 (2010). [Russ. J. Org. Chem., 46, 1822 (2010).]Google Scholar
  12. 12.
    H.-M. Chen, P.-Y. Chen, C. -F. Wang, J.-C. Tsai, and E.-C. Wang, ARKIVOC, viii, 157 (2012).Google Scholar
  13. 13.
    P. M. Heertjes and L. J. Revallier, Rec. Trav. Chim. Pays-Bas, 69, 262 (1950).CrossRefGoogle Scholar
  14. 14.
    Z. Huang and G. Zhou, EP Pat. Appl. 2532665.Google Scholar
  15. 15.
    A. Krasso and H. Ramuz, CH Pat. Appl. 644116.Google Scholar
  16. 16.
    N. I. Korotkikh, G. F. Raenko, A. F. Aslanov, and O. P. Shvaika, Khim. Geterotsikl. Soedin., 706 (1994). [Chem. Heterocycl. Compd., 30, 621 (1994)].Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • M. A. Orlov
    • 1
  • I. V. Kapitanov
    • 1
  • N. I. Korotkikh
    • 1
  • O. P. Shvaika
    • 1
  1. 1.L. M. Litvinenko Institute of Physical Organic and Coal ChemistryDonetskUkraine

Personalised recommendations