Recent Advances in the Synthesis of Benzimidazol-2-ones via Rearrangements

Synthesis of Morpholine-, Piperidine-, and N-Substituted Piperazine-Coupled 2-(Benzimidazol-2-yl)-3-arylquinoxalines as Novel Potent Antitumor Agents

“…The synthesis of three types of new regioisomeric derivatives of 2-(benzimidazol-2-yl)­quinoxaline 13 and 14 containing, in position 6 or 7, 4-methylpiperazine, 4-phenylpiperazine (Table , entries 1–5 and 6) (type I), piperidine (Table , entries 7 and 8) (type II), and morpholine (Table , entries 9 and 10) (type III) fragments, was carried out via Mamedov rearrangement − by the interaction of 3-aroylquinoxalinones 9a – 9f with benzene-1,2-diamines 12a – 12d at reflux in acetic acid for 4 h. Along with the target products 13ea, 14ea (Table , entry 5) and 13ed , 14ed (Table , entry 10), byproducts 15ea , 16ea and 15ed , 16ed are formed, respectively (Figure ), as a result of nucleophilic substitution of the fluorine atom of the aryl ring with the nitrogen atom of the benzimidazole system; , mixtures of regioisomers 15ea / 16ea and 15ed / 16ed were isolated by column chromatography. The structures of compounds 13da and 14da were confirmed by the single-crystal X-ray analysis (Figure ), and the phase state of a powder mixture of these regiosomers was analyzed by powder X-ray diffraction (see Supporting Information).…”

“…To check these binding interactions and antitumor activity of a novel series of regioisomeric 2-(benzimidazol-2-yl)-3-arylquinoxalines designed using a concept of molecular hybridization with the mentioned substituents in positions 6 and 7 of the benzene ring of the quinoxaline system, we studied the reactivity of 3-aroylquinoxalinones with respect to specially synthesized benzene-1,2-diamines with N -methyl, N -phenylpiperazine, piperidine, and morpholine substituents in position 4 of the benzene ring under Mamedov rearrangement − conditions.…”

Bimetallic Cu–Ni Nanometal Supported over Mesocellular Silica Foam As a Novel Catalyst for One-Pot Synthesis of Benzimidazole in DMF As a Bifunctional Reagent

“…Watercolor paintings and electrophotographic developing toner have been prepared using benzimidazole derivatives for a very long time due to their light resistance and durability. 22 Moreover, benzimidazole is an important core molecule in organic light-emitting devices (OLEDs), having good thermal properties, phosphorescence, and stability of the morphological structures. 23−25 The foregoing amply demonstrates that benzimidazole is a very important and versatile chemical moiety, and its synthesis and use in chemical industries and applications can be assumed to be a never-ending process (Figure 1).…”

“…Similarly, the literature also reports the use of common benzimidazoles as insecticides, pesticides, and herbicides. − Benzimidazole derivatives have been explored as potential corrosion inhibitors for metals like Cu, Fe, and Zn under acidic conditions. − Researchers have also studied the use of benzimidazoles as essential chromophores in organic dyes due to their molecular physical and chemical properties. Watercolor paintings and electrophotographic developing toner have been prepared using benzimidazole derivatives for a very long time due to their light resistance and durability . Moreover, benzimidazole is an important core molecule in organic light-emitting devices (OLEDs), having good thermal properties, phosphorescence, and stability of the morphological structures. − …”

Bromine-Promoted One-Pot Furo[b]annulation and α-C(sp2)-Thiomethylation Cascade of (E)-3-Styrylquinoxalin-2(1H)-ones with Dimethyl Sulfoxide

“…In connection with our interest in the synthesis of fused heterocyclic systems − based on functionalized quinoxalin-2­(1 H )-one derivatives, we present here the synthesis and complete characterization of the new furo­[2,3- b ]­quinoxaline derivatives by bromine-mediated one-pot efficient furo­[ b ]­annulation and α-C­(sp 2 )-thiomethylation cascades of ( E )-3-styrylquinoxalin-2­(1 H )-ones with DMSO. The furo­[2,3- b ]­quinoxaline derivatives showed promising pharmacological properties as the potential inhibitors of sirtuins and were significant for the inhibition of the growth of human cervical cancer (Hela) and hepatocellular liver carcinoma (HepG2) cells .…”