6478-80-4Relevant articles and documents
Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon
Raja, Dineshkumar,Philips, Abigail,Sundaramurthy, Devikala,Chandru Senadi, Gopal
supporting information, p. 3754 - 3759 (2021/10/14)
D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.
BOIMPYs: Rapid Access to a Family of Red-Emissive Fluorophores and NIR Dyes
Patalag, Lukas J.,Jones, Peter G.,Werz, Daniel B.
supporting information, p. 13340 - 13344 (2016/10/30)
A fundamental, highly fluorescent, and easily accessible scaffold derived from the BODIPY core is reported. The use of benzimidazole as a bridging ligand at the meso position enables the binding of two BF2units to provide sufficient rigidity and enhanced electron-withdrawing strength. Absorption and emission events thus take place in the red (λ≈600 nm); the fluorescence quantum yields can reach unity (0.96) and show little dependence on solvent polarity. The synthetic route was shortened to two steps starting from commercially available precursors while the preparation is modular and tolerates various pyrrole and benzimidazole moieties. Fluoride replacement by propynyl groups, various halogenations, as well as Knoevenagel-type condensations were applied to extend the versatility of these new photostable fluorophores, which we termed BOIMPYs.
