Skip to main content
SpringerLink
Log in

Condensation of 5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione with haloacetic acids

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Reactions of triazolethiones with haloacetic acids were studied with 5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione as an example. It was proved for the first time by X-ray diffraction that the cyclocondensation of these compounds proceeds regiospecifically to give 2-(4-methylphenyl)[1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-one rather than its isomer 3-(4-methylphenyl)[1,3]thiazolo[2,3-c][1,2,4]triazol-5(6H)-one.

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. H. H. Sayed, E. M. H. Morsy, E. M. Flefel, Synth. Commun., 2010, 40, 1360.

    Article  CAS  Google Scholar 

  2. P. M. Veeresha Sharma, M. G. Purohit, Synth. Commun., 2008, 38, 1381.

    Article  CAS  Google Scholar 

  3. E. G. Knysh, I. A. Mazur, V. S. Zimenkovskii, V. R. Stets, V. V. Dunaev, P. N. Steblyuk, Khim.-Farm. Zh., 1984, 18, 1324 [Pharm. Chem. J. (Engl. Transl.), 1984, 18, 765].

    CAS  Google Scholar 

  4. M. Jankulovska, L. Š optrajanova, I. Spirevska, K. Čolančevska-Ragenovik, S. Ristovski, Maced. J. Chem. Chem. Eng., 2010, 29, 43.

    CAS  Google Scholar 

  5. US Pat. 7732374 B2, 2010; books.google.com/patents/US7732374.pdf.

  6. Ch. Eui Song, Ji-S. Kim, J. H. Choi, B. W. Jin, Heterocycles, 1999, 51, 161.

    Article  CAS  Google Scholar 

  7. B. V. Trzhtsinskaya, E. I. Kositsina, B. Z. Pertsikov, E. V. Rudakova, V. K. Voronov, G. G. Skvortsova, Khim. Geterotsikl. Soedin., 1987, 23, 271 [Chem. Heterocycl. Compd. (Engl. Transl.), 1987, 23, 228].

    Google Scholar 

  8. A. A. Shklyarenko, D. G. Nasledov, V. V. Yakovlev, Zh. Org. Khim., 2005, 41, 636 [Russ. J. Org. Chem. (Engl. Transl.), 2005, 41, 627].

    Google Scholar 

  9. Zh. Wang, Haoxin Shi, Haijian Shi, Synth. Commun., 2001, 31, 2841.

    Article  CAS  Google Scholar 

  10. T. Cablewski, C. L. Francis, A. J. Liepa, Aust. J. Chem., 2008, 61, 332.

    Article  CAS  Google Scholar 

  11. V. N. Britsun, A. N. Esipenko, A. N. Chernega, M. O. Lozinskii, Zh. Org. Khim., 2005, 41, 109 [Russ. J. Org. Chem. (Engl. Transl.), 2005, 41, 108].

    Google Scholar 

  12. S. Kumar, R. Dahiya, D. M. Puri, H. K. Pujari, Indian J. Chem., Sect. B, 1991, 30, 38.

    Google Scholar 

  13. B. Tozkoparan, H. Akgün, M. Ertan, K. Rübsemann, Arch. Pharm., 1995, 328, 169.

    Article  CAS  Google Scholar 

  14. B. K. Garnaik, M. Sahu, R. K. Behera, A. Nayak, J. Indian Chem. Soc., 1989, 67, 832.

    Google Scholar 

  15. M. Sahu, A. Nayak, J. Indian Chem. Soc., 1990, 67, 226.

    CAS  Google Scholar 

  16. M. Sen, N. Mishra, A. Nayak, J. Indian Chem. Soc., 1990, 67, 409.

    CAS  Google Scholar 

  17. G. I. Chipen, D. E. Duka, V. Ya. Grinshtein, Khim. Geterotsikl. Soedin., 1966, 2, 84 [Chem. Heterocycl. Compd. (Engl. Transl.), 1966, 2, 117].

    Google Scholar 

  18. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1.

    Google Scholar 

  19. APEX2 and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA, 2005.

  20. G. M. Sheldrick, Acta Crystallogr., Sect. A, 2008, 64, 112.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Yaroslavl State Technical University, 88 Moskovskii pr., 150023, Yaroslavl, Russian Federation

    A. A. Rzhevskii, N. P. Gerasimova, E. M. Alov, O. S. Kozlova & A. S. Danilova

  2. Yaroslavl State Academy of Agriculture, 58 Tutaevskoe sh., 150042, Yaroslavl, Russian Federation

    S. A. Khapova

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. Yu. Suponitskii

Authors
  1. A. A. Rzhevskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. P. Gerasimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. M. Alov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. S. Kozlova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. S. Danilova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. A. Khapova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. K. Yu. Suponitskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. A. Rzhevskii.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2116–2119, November, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rzhevskii, A.A., Gerasimova, N.P., Alov, E.M. et al. Condensation of 5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione with haloacetic acids. Russ Chem Bull 61, 2133–2136 (2012). https://doi.org/10.1007/s11172-012-0299-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-012-0299-8

Key words

Search

Navigation