2562-81-4Relevant articles and documents
Synthesis and Tautomerism of 2-Aryl- and 2-Heteroaryl Derivatives of Benzimidazole
Lee, In-Sook Han,Jeoung, Eun Hee,Lee, Chang Kiu
, p. 1711 - 1716 (1996)
Benzimidazoles containing furyl and thienyl substituents at C-2 were prepared by condensation of o-phenylenediamine and corresponding carboxylic acids in the presence of polyphosphoric acid. The 2-heteroarylbenzimidazoles showed tautomerism in dimethyl sulfoxide solution while 2-phenylbenzimidazole did not. The tautomerism appeared to be taking place by intermolecular relay of protons between stacked molecules.
Coordination mode-induced isomeric cyclometalated [Ir(tpy)(nbi)Cl](PF6) complexes: Distinct luminescence, self-assembly and cellular imaging behaviors
Gao, Tai-Bao,Yan, Run-Qi,Metherell, Alexander J.,Cao, Deng-Ke,Ye, De-Ju,Ward, Michael D.
, p. 16787 - 16791 (2017)
Two isomeric Ir(iii) complexes Ir-O and Ir-R arising from the different coordination mode of a naphthalene-containing ligand, show distinct luminescence, self-assembly ability and cellular imaging behaviors.
An Unexpected Formation of 2-Arylbenzimidazoles from α,α-Diiodo-α’-acetoxyketones and o-Phenylenediamines
Sadhukhan, Santu,Mondal, Swagata,Baire, Beeraiah
, (2022/03/01)
An unusual reactivity of the α,α-diiodo-α’-acetoxyketones with o-phenylenediamines is reported through the formation of 2-arylbenzimidazoles. A systematic study through a series of fruitful control experiments and isolation of key intermediates unravelled the unprecedented domino mechanism. This process involves a stepwise two-carbon fragmentation pathway through domino and sequential amidation–aziridination–decarbonylation–I2-mediated aminative cyclization–oxidation reactions. This strategy employs no additives like oxidant, metal catalyst, bases, and represents yet another novel reactivity profile of the building blocks α,α-diiodo-α’-acetoxyketones.
A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles
Kumar, Sonu,Sarmah, Manash P.,Reddy, Yella,Bhatt, Ashish,Kant, Ravi
, p. 96 - 105 (2021/11/23)
Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation of N-hydroxy intermediate, which at higher temperature cleaves to afford the desired product. This approach achieved reductions in reaction times, higher yields, cleaner reactions than the previously described synthetic processes.
