Skip to main content
SpringerLink
Log in

Study of the Products of Iodocyclization of 4-Allyl-5-phenyl-1,2,4-triazole-3-thione

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The interaction of 4-allyl-5-phenyl-1,2,4-triazole-3-thione with iodine proceeds with the formation of a mixture of 6-iodomethyl-3-phenyl-5,6-dihydrothiazolo[2,3-c]-1,2,4-triazole and 6-iodo-3-phenyl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b]-1,3-thiazine. The structures of the cyclization products obtained were established on the basis of the 1H NMR spectra of their dehydroiodinated derivatives. 6-Methyl-3-phenylthiazolo[2,3-c]-1,2,4-triazole, 3-phenyl-5H-1,2,4-triazolo[3,4-b]-1,3-thiazine, and 3-phenyl-7H-1,2,4-triazolo[3,4-b]-1,3-thiazine are formed on eliminating HI from the cyclization products.

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. M. N. Tsitsika, S. M. Khripak, and I. V. Smolanka, Ukr. Khim. Zh., 42, 841 (1976).

    Google Scholar 

  2. S. Ernst, S. Jelonek, J. Silez, and K. Schulze, Tetrahedron, 52, 791 (1996).

    Google Scholar 

  3. L. Strzemecka, Polish J. Chem., 57, 567 (1983).

    Google Scholar 

  4. M. Tamaru and Z. Yoshida, J. Org. Chem., 50, 764 (1985).

    Google Scholar 

  5. D. G. Kim and V. I. Shmygarev, Khim. Geterotsikl. Soedin., 211 (1995).

  6. P. Wippich, C. Hendreich, M. Gutshow, and S. Leistner, Synthesis, 741 (1996).

  7. B. I. Ionin, B. A. Ershov, and A. I. Kol'tsov, NMR Spectroscopy in Organic Chemistry [in Russian], Khimiya, Leningrad (1983).

    Google Scholar 

  8. K. T. Potts and S. Husain, J. Org. Chem., 36, 10 (1971).

    Google Scholar 

  9. Y. Tamura, H. Hayashy, J. H. Kim, and M. Ikeda, J. Heterocycl. Chem., 10, 947 (1973).

    Google Scholar 

  10. Y. Tamura, H. Hayashy, E. Saeki, J. H. Kim, and M. Ikeda, J. Heterocycl. Chem., 11, 459 (1974).

    Google Scholar 

  11. V. P. Upadhyaya, T. G. S. Nath, and V. R. Srinivasan, Synthesis, 283 (1978).

Download references

Author information

Authors and Affiliations

  1. Chelyabinsk State University, Chemical Faculty, Chelyabinsk, 454021, Russia

    V. I. Shmygarev & D. G. Kim

Authors
  1. V. I. Shmygarev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. G. Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shmygarev, V.I., Kim, D.G. Study of the Products of Iodocyclization of 4-Allyl-5-phenyl-1,2,4-triazole-3-thione. Chemistry of Heterocyclic Compounds 40, 1077–1082 (2004). https://doi.org/10.1023/B:COHC.0000046700.89050.90

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:COHC.0000046700.89050.90

Search

Navigation