Skip to main content
SpringerLink
Log in

Competition of the Hantzsch and boese reactions in the interaction of 1-thiocarbamoylthiosemicarbazide and phenylchloropyruvic acid methyl ester

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1-Thiocarbamoylthiosemicarbazide, the synthetic equivalent of thiourea and thiosemicarbazide, reacts with phenylchoropyruvic acid methyl ester exclusively as thiourea (Hantzsch reaction) forming 2-hydrazo-4-methoxycarbonyl-5-phenylthiazole. Diacetylation and reductive fission of this hydrazo compound was carried out, and also oxidation to the corresponding azo compound, readily accomplished with using dimethyl sulfoxide.

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. V. A. Mamedov and I. A. Nuretdinov,Izv. Akad. Nauk, Ser. Khim., No. 9, 2159 (1992).

    Google Scholar 

  2. V. A. Mamedov, I. A. Nuretdinov, and F. G. Sibgatullina,Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2172 (1988).

    Google Scholar 

  3. V. A. Mamedov and I. A. Nuretdinov,Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2856 (1987).

    Google Scholar 

  4. V. A. Mamedov, I. A. Nuretdinov, and D. I. Sadkova,Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2854 (1990).

    Google Scholar 

  5. V. A. Mamedov, I. A. Nuretdinov, and F. G. Sibgatullina,Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2832 (1991).

    Google Scholar 

  6. V. A. Mamedov, V. N. Valeeva, L. A. Antokhina, and I. A. Nuretdinov,Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1422 (1991).

    Google Scholar 

  7. V. A. Mamedov, I. A. Litvinov, Yu. Ya. Efremov, V. N. Valeeva, I. Kh. Rizvanov, O. N. Kataeva, L. A. Antokhina, and I. A. Nuretdinov,Zh. Org. Khim.,29, 1042 (1993).

    Google Scholar 

  8. V. A. Mamedov, E. A. Berdnikov, V. N. Valeeva, I. E. Ismaev, I. Kh. Rizvanov, L. A. Antokhina, I. A. Nuretdinov, and P. P. Chernov,Izv. Akad. Nauk, Ser. Khim., No. 11, 1962 (1993).

    Google Scholar 

  9. V. A. Mamedov, L. V. Krokhina, E. A. Berdnikov, and Ya. A. Levin,Khim. Geterotsikl. Soedin., No. 9, 1266 (1996).

    Google Scholar 

  10. V. A. Mamedov and I. A. Nuretdinov,Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1670 (1988).

    Google Scholar 

  11. V. A. Mamedov, F. G. Sibgatullina, V. P. Gubskaya, R. M. Gainullin, R. R. Shagidullin, and A. V. Il'yasov,Khim. Geterotsikl. Soedin., No. 9, 1191 (1994).

    Google Scholar 

  12. V. A. Mamedov, V. N. Valeeva, F. G. Sibgatullina, L. A. Antokhina, and I. A. Nuretdinov,Khim. Geterotsikl. Soedin., No. 2, 250 (1993).

    Google Scholar 

  13. M. Kurahashi,Bull. Chem. Soc. Japan,49, No. 11, 2927 (1976).

    Google Scholar 

  14. C. J. Brown,Acta Crystallogr.,21, 146 (1966).

    Article  Google Scholar 

  15. C. J. Brown,Acta Crystallogr.,21, 153 (1966).

    Article  Google Scholar 

  16. A. Altomare, G. Cascarano, C. Giacovazzo, and D. Viterbo,Acta Crystallogr. A,47, 744 (1991).

    Article  Google Scholar 

  17. L. H. Straver and A. J. Schierbeek,MolEN. Structure Determination System. Vol. 1. Program Description, Nonius B. V., Delft (1994).

    Google Scholar 

Download references

Authors
  1. V. A. Mamedov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. Z. Nurkhametova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. T. Gubaidullin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. A. Litvinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ya. A. Levin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan 420088; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1554–1560, November, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mamedov, V.A., Nurkhametova, I.Z., Gubaidullin, A.T. et al. Competition of the Hantzsch and boese reactions in the interaction of 1-thiocarbamoylthiosemicarbazide and phenylchloropyruvic acid methyl ester. Chem Heterocycl Compd 35, 1357–1363 (1999). https://doi.org/10.1007/BF02252009

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02252009

Keywords

Search

Navigation