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

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.

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References

  1. 1.

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

  2. 2.

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

  3. 3.

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

  4. 4.

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

  5. 5.

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

  6. 6.

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

  7. 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).

  8. 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).

  9. 9.

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

  10. 10.

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

  11. 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).

  12. 12.

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

  13. 13.

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

  14. 14.

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

  15. 15.

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

  16. 16.

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

  17. 17.

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

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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.

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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

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Keywords

  • Oxidation
  • Methyl
  • Ester
  • Organic Chemistry
  • Methyl Ester