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Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80
Graphical Abstract
Figure 1: Examples of natural and synthetic bioactive 1,3-thiazine and imidazothiazolotriazine derivatives wi...
Scheme 1: Base-induced transformations and rearrangements of functionalized imidazo[4,5-e]thiazolo[3,2-b]-1,2...
Scheme 2: Alkaline hydrolysis of esters 1a,b. aDetermined by 1H NMR spectroscopy; bisolated yields.
Scheme 3: Synthesis of potassium imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylates.
Scheme 4: Plausible rearrangement mechanism of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine 1d into imidazo[4...
Figure 2: 1H NMR spectra of the starting compound 1d (a) and the reaction mixture after 1.5 (b) and 4 (c) hou...
Scheme 5: Synthetic approaches to imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines 3a–d,j.
Scheme 6: Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylic acids 5a–j.
Scheme 7: Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylic acids 5k,m.
Scheme 8: Plausible path for the formation of products 9.
Figure 3: 1H NMR spectra of compounds 4a and 5a in DMSO-d6 in the region of 4.3–9.0 ppm.
Figure 4: 13C NMR GATED spectra of compounds 4a and 5a in DMSO-d6 in the region of 156.0–168.0 ppm.
Figure 5: General view of 5a in the crystal in thermal ellipsoid representation (p = 80%).
Beilstein J. Org. Chem. 2021, 17, 1141–1148, doi:10.3762/bjoc.17.87
Figure 1: Biologically active compounds having thiazolidin-4-one and thiazolo-1,2,4-triazine units.
Scheme 1: Regioselectivity of the cyclization of 3-thioxo-1,2,4-triazin-5-ones 1 with DMAD (A) and general co...
Scheme 2: Synthesis of imidazo[4,5-e]thiazolo[3,2-b]triazine derivatives 4a–n by the reaction of imidazo[4,5-...
Scheme 3: Reaction of imidazo[4,5-e]thiazolo[3,2-b]triazine 4h with aqueous KOH.
Scheme 4: Rearrangement of imidazo[4,5-e]thiazolo[3,2-b]triazines 4a–n into imidazo[4,5-e]thiazolo[2,3-c]tria...
Scheme 5: One-pot synthesis of compounds 5a,b,h,i from imidazo[4,5-e]triazines 3a,b.
Scheme 6: Plausible mechanism of the formation and the rearrangement of compounds 4 into isomers 5.
Figure 2: 1H NMR spectra of compounds 4h and 5h in DMSO-d6 in the region of 3.5–8.8 ppm.
Figure 3: X-ray crystal structure of compound 5i.
Beilstein J. Org. Chem. 2016, 12, 2240–2249, doi:10.3762/bjoc.12.216
Figure 1: Bioactive 2,3’-spiropyrrolidinyloxindoles.
Scheme 1: Earlier studied cycloaddition reaction.
Scheme 2: Synthesis of dipolarophiles 1a–c.
Scheme 3: Synthesis of dispirocompounds 4a–o.
Figure 2: Synthesis of dispiro compounds 4a–o. Reaction conditions: heating the mixture of compounds 1 (0.5 m...
Scheme 4: Synthesis of dipolarophiles 1d–f.
Figure 3: Synthesis of dispiro compounds 4p–t. Reaction conditions: heating the solution of compounds 1 (0.5 ...
Figure 4: Key interactions in {1H-13C}HMBC spectrum of 4f.
Figure 5: General view of 4c in the crystal in thermal ellipsoids representation (50% probability). Hydrogen ...
Figure 6: General view of 4e in the crystal in thermal ellipsoids representation (40% probability). Hydrogen ...
Figure 7: General view of 4r in the crystal in thermal ellipsoids representation (50% probability). Hydrogen ...
Figure 8: Modes of approach of azomethine ylide (R = H, Ph).