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Synthesis and biological activity of oxindolylidene derivatives of imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-7-ones and imidazo[4,5-e]thiazolo[2,3-с]-1,2,4-triazin-8-ones

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Abstract

Reactions of 1,3-dialkyl-2-thioxo-1,2,3,3a,9,9a-hexahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-7(6H)-ones with isatin and its derivatives under base catalysis conditions lead to the corresponding 1,3-dialkyl-6(7)-(2-oxoindolin-3-ylidene)derivatives of 2-thioxo-1,2,3,3a,9,9a-hexahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-7(6H)-one or 2-thioxo-1,2,3,3a,4,9a-hexahydroimidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazin-8(7H)-one resulting from the aldol-crotonic condensation and skeletal amidine rearrangement of the thiazolotriazine fragment, depending on the amount of added alkali.

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Authors and Affiliations

  1. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    A. N. Izmest’ev, G. A. Gazieva, A. S. Kulikov, N. G. Kolotyrkina & A. N. Kravchenko

  2. Institute of Physiologically Active Substances, Russian Academy of Sciences, Chernogolovka, Moscow oblast, Russia

    L. V. Anikina

Authors
  1. A. N. Izmest’ev
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  2. G. A. Gazieva
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  3. A. S. Kulikov
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  4. L. V. Anikina
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  5. N. G. Kolotyrkina
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  6. A. N. Kravchenko
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Corresponding author

Correspondence to G. A. Gazieva.

Additional information

Original Russian Text © A.N. Izmest’ev, G.A. Gazieva, A.S. Kulikov, L.V. Anikina, N.G. Kolotyrkina, A.N. Kravchenko, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 5, pp. 741–750.

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Izmest’ev, A.N., Gazieva, G.A., Kulikov, A.S. et al. Synthesis and biological activity of oxindolylidene derivatives of imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-7-ones and imidazo[4,5-e]thiazolo[2,3-с]-1,2,4-triazin-8-ones. Russ J Org Chem 53, 753–763 (2017). https://doi.org/10.1134/S1070428017050177

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  • DOI: https://doi.org/10.1134/S1070428017050177

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