Investigation of the halocyclization of S- and N-allyl derivatives of 2-benzothiazolethione

  • D. G. Kim
  • N. M. Sudolova
  • P. A. Slepuhin

3-Allyl-2-benzothiazolethione reacts with iodine regiospecifically with annelation of the five-membered ring, while with bromine a mixture of the five- and six-membered rings are formed. 2-Allylthioben- zothiazole reacts with halogens with annelation of the five- and six-membered rings, while 2-(2-methyl-2-propenyl)thiobenzothiazole is annelated at the five-membered ring.


2- and 3-halomethyl-2,3-dihydrothiazolo[2,3-b]benzothiazolium halides 3-halo-3,4-dihyd- ro-2H-[1,3]thiazino[2,3-b][1,3]benzothiazolium halocyclization X-ray crystallography 


  1. 1.
    M. Kocevar, B. Stanovnik, and M. Tisler, Croat. Chem. Acta, 45, 457 (1973).Google Scholar
  2. 2.
    N. I. Korotkikh, A. F. Aslanov, and O. P. Shvaika, Khim. Geterotsikl. Soedin., 855 (1990). [Chem.Heterocycl. Comp., 26, 716 (1990)].Google Scholar
  3. 3.
    D. G. Kim, Khim. Geterotsikl. Soedin., 556 (1998). [Chem. Heterocycl. Comp., 34, 505 (1998)].Google Scholar
  4. 4.
    K. Undheim and K. R. Reistad, Acta. Chem. Scand., 24, 2949 (1970).CrossRefGoogle Scholar
  5. 5.
    A. M. Shestopalov, M. A. Rodinovskaya, Yu. A. Sharanin, and V. P. Litvinov, Khim. Geterotsikl. Soedin., 256 (1990). [Chem. Heterocycl. Comp., 26, 221 (1990)].Google Scholar
  6. 6.
    D. G. Kim, Khim. Geterotsikl. Soedin., 334 (1999). [Chem. Heterocycl. Comp., 35, 290 (1999)].Google Scholar
  7. 7.
    D. G. Kim, N. M. Sudolova, P.A. Slepuhin, and V. N. Charushin, Khim. Geterotsikl. Soedin., 1744 (2010). [Chem. Heterocycl. Comp., 46, 1420 (2010)].Google Scholar
  8. 8.
    R. C. Clark and J. S. Reid, Acta Crystallogr., A51, 887 (1955).Google Scholar
  9. 9.
    G. M. Sheldrick, Acta Crystallogr., A64, 112 (2008).Google Scholar
  10. 10.
    V. L. Lapenko, L. M. Pavlov, and G. V. Shatalov, Handbook on the Synthesis of Polymerization monomers and High-molecular Compounds, [in Russian]. Izd-vo Voronezh. Un-ta, Voronezh, 1983, p. 105.Google Scholar
  11. 11.
    T. Takahashi, K. Aritsune, and H. Jun-ichi, Bull. Inst., Chem. Res., Kyoto Univ., 163 (1979).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  1. 1.South Ural State UniversityChelyabinskRussia
  2. 2.I. Ya. Postovskii Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia

Personalised recommendations