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Beilstein J. Org. Chem. 2021, 17, 1141–1148, doi:10.3762/bjoc.17.87
Graphical Abstract
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.