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Beilstein J. Org. Chem. 2019, 15, 1962–1973, doi:10.3762/bjoc.15.191
Graphical Abstract
Figure 1: Examples of some commercially available pharmaceuticals and agrochemicals containing the benzimidaz...
Figure 2: Formation of cationic species by protonation of 5-formyl-4-methylimidazole in TfOH and their reacti...
Figure 3: Benzimidazoles 1–8 used in this study.
Scheme 1: Reaction of 2-acetylbenzimidazole (2) with TfOH and benzene.
Scheme 2: Reactions of hydroxymethyl-substituted benzimidazole 7 and 8 with TfOH and benzene.
Scheme 3: Reaction mechanism of the formation of compounds 9–11.
Scheme 4: Reaction mechanism of the formation of compounds 12.
Beilstein J. Org. Chem. 2016, 12, 2125–2135, doi:10.3762/bjoc.12.202
Figure 1: Formation of 5-HMF from D-glucose or D-fructose followed by oxidation to 2,5-DFF.
Scheme 1: Protonation of 5-HMF (1a) and 2,5-DFF (2) leading to cationic species A, B, C, D.
Figure 2: X-ray crystal structure of compounds 5a (a), and 5c (b) (ORTEP diagrams, ellipsoid contour of proba...