Halogenation of Substituted Benzimidazoles. Nitration of the Resulting Halobenzimidazoles

Predictive Model for Site-Selective Aryl and Heteroaryl C–H Functionalization via Organic Photoredox Catalysis

“…Again, the predictive model accurately foretold the major products of these heterocycles on the basis of the largest NPA difference. The sites of functionalization for benzazoles correlate well with E A S site selectivity, , similarly to the six-membered aromatic compounds discussed previously. Though the computational model was needed to understand the origins of the site selectivity, the analogy to E A S regioselectivity can be used as a strategy to predict the site selectivity in many cases.…”

Steering Self-Assembly of Amphiphilic Molecular Nanostructures via Halogen Exchange

“…2-Methylbenzimidazole ( 1 ) was converted into 5,6-dibromo-2-methylbenzimidazole ( 2 ), by bromination with NBS according to the modified literature procedure. 45 Selective bromination was achieved at the 5 and 6 positions, and pure compound was obtained in 55% yield after crystallization in toluene. The corresponding benzimidazole was then treated with 1-bromooctane in the presence of KOH to obtain 5,6-dibromo-2-methyl-1-octyl-benzimidazole ( 3 ), in almost quantitative yield after work up.…”

“…2-Methylbenzimidazole ( 1 ) was converted into 5,6-dibromo-2-methylbenzimidazole ( 2 ), by bromination with NBS according to the modified literature procedure . Selective bromination was achieved at the 5 and 6 positions, and pure compound was obtained in 55% yield after crystallization in toluene.…”

6-Nitro-1,3-benzoxazole-2(3H)-thione

“…The mono-nitration of some benzimidazole derivatives has been reported (Benchidmi et al, 1995;El Kihel et al, 1999). In this work, the nitration of benzoxazole-2-thione has been carried out and the crystal structure determined to establish the location of the NO 2 group (the 5-or 6-position) in the product (Fig.…”