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Synthesis of 5-arylmethylidene-3-(arylmethylideneamino)thiazolidine-2,4-diones via triazine ring cleavage of tetrahydroimidazothiazolotriazinediones and their reactions with azomethine ylides

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Chemistry of Heterocyclic Compounds Aims and scope

Cleavage of 1,3-dimethyl-3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-2,7(1H,6H)-diones upon treatment with aromatic aldehydes has been shown to afford (Z)-5-arylmethylidene-3-((E)-arylmethylideneamino)thiazolidine-2,4-diones bearing two identical or different arylmethylidene fragments at the exocyclic nitrogen atom and at position 5 of thiazolidine cycle. 1,3-Dipolar cycloaddition reaction of thiazolidine-2,4-dione derivatives with azomethine ylide generated from isatin and sarcosine gave diastereomerically pure dispiro[indole-3,2′-pyrrolidine-3′,5″-thiazolidine]-2,2″,4″-triones in good yields. Dispiro compound with two 4-methoxyphenyl fragments exhibited slight antiproliferative activity toward CCRF-CEM (leukemia) and CAKI-1 (renal cancer) cell lines.

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Scheme 1.
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The reported study was funded by Russian Foundation for Basic Research (project No. 20-03-00765).

Crystal structure determination was performed in the Department of Structural Studies of N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences.

The authors would like to thank Dr. Yu. A. Strelenko (N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences) for 2D NMR experiments.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Alexei N. Izmest’ev, Galina A. Gazieva, Natalya G. Kolotyrkina, Elena D. Daeva & Angelina N. Kravchenko

  2. National University of Science and Technology (MISiS), 4 Leninsky Ave., Moscow, 119049, Russia

    Alexei N. Izmest’ev

  3. Plekhanov Russian University of Economics, 36 Stremyanny Lane, Moscow, 117997, Russia

    Angelina N. Kravchenko

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  1. Alexei N. Izmest’ev
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  2. Galina A. Gazieva
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Correspondence to Galina A. Gazieva.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(12), 1569–1578

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Izmest’ev, A.N., Gazieva, G.A., Kolotyrkina, N.G. et al. Synthesis of 5-arylmethylidene-3-(arylmethylideneamino)thiazolidine-2,4-diones via triazine ring cleavage of tetrahydroimidazothiazolotriazinediones and their reactions with azomethine ylides. Chem Heterocycl Comp 56, 1569–1578 (2020). https://doi.org/10.1007/s10593-020-02851-w

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