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Annelation of the thiazole ring to 1,2,4-triazines by tandem AN—AN or SN H—SN H reactions

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Abstract

The reactions of 3-aryl-1,2,4-triazines with aromatic thioamides and 4-arylthiosemicarbazides in acetic anhydride at room temperature afforded cyclic products of the tandem nucleophilic addition reactions, viz., tetrahydrothiazolo[4,5-e]-annelated 1,2,4-triazines, in good yields. The latter underwent aromatization in the presence of potassium permanganate.

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Authors and Affiliations

  1. Urals State Technical University, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation, Russia

    N. N. Mochul"skaya

  2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219 Ekaterinburg, Russian Federation, Russia

    A. A. Andreiko, M. I. Kodess, E. B. Vasil"eva, V. I. Filyakova & V. N. Charushin

  3. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation, Russia

    A. T. Gubaidullin, I. A. Litvinov & O. G. Sinyashin

  4. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991 Moscow, Russian Federation, Russia

    G. G. Aleksandrov

Authors
  1. N. N. Mochul"skaya
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  2. A. A. Andreiko
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  3. M. I. Kodess
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  4. E. B. Vasil"eva
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  5. V. I. Filyakova
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  6. A. T. Gubaidullin
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  7. I. A. Litvinov
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  8. O. G. Sinyashin
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  9. G. G. Aleksandrov
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  10. V. N. Charushin
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Mochul"skaya, N.N., Andreiko, A.A., Kodess, M.I. et al. Annelation of the thiazole ring to 1,2,4-triazines by tandem AN—AN or SN H—SN H reactions. Russian Chemical Bulletin 53, 1279–1289 (2004). https://doi.org/10.1023/B:RUCB.0000042287.32992.54

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  • DOI: https://doi.org/10.1023/B:RUCB.0000042287.32992.54

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