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1 article(s) from Strelenko, Yuri A

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

Dmitry B. Vinogradov,
Alexei N. Izmest’ev,
Angelina N. Kravchenko,
Yuri A. Strelenko and
Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

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Figure 1: Examples of natural and synthetic bioactive 1,3-thiazine and imidazothiazolotriazine derivatives wi...

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Scheme 1: Base-induced transformations and rearrangements of functionalized imidazo[4,5-e]thiazolo[3,2-b]-1,2...

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Scheme 2: Alkaline hydrolysis of esters 1a,b. ^aDetermined by ¹H NMR spectroscopy; ^bisolated yields.

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Scheme 3: Synthesis of potassium imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylates.

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Scheme 4: Plausible rearrangement mechanism of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine 1d into imidazo[4...

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Figure 2: ¹H NMR spectra of the starting compound 1d (a) and the reaction mixture after 1.5 (b) and 4 (c) hou...

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Scheme 5: Synthetic approaches to imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines 3a–d,j.

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Scheme 6: Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylic acids 5a–j.

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Scheme 7: Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylic acids 5k,m.

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Scheme 8: Plausible path for the formation of products 9.

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Figure 3: ¹H NMR spectra of compounds 4a and 5a in DMSO-d₆ in the region of 4.3–9.0 ppm.

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Figure 4: ¹³C NMR GATED spectra of compounds 4a and 5a in DMSO-d₆ in the region of 156.0–168.0 ppm.

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Figure 5: General view of 5a in the crystal in thermal ellipsoid representation (p = 80%).

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Published 28 Jul 2023

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