Benzimidazole

Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and imidazole. The most prominent benzimidazole compound in nature is N-ribosyl-dimethylbenzimidazole, which serves as an axial ligand for cobalt in vitamin B12. ^[1]

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It is produced commercially as an parasiticide. The usual synthesis involves condensation of trimethylorthoformate and o-phenylenediamine:

C₆H₄(NH₂)₂ + HC(OCH₃)₃ → C₆H₄N(NH)CH + 3 CH₃OH

Benzimidazole, in an extension of the well-elaborated imidazole system, has been used as carbon skeletons for N-heterocyclic carbenes. The NHCs are usually used as ligands for transition metal complexes. They are often prepared by deprotonating an N,N'-disubstituted benzimidazolium salt at the 2-position with a base.^[2][3]

See also

• Albendazole, a common use anthelmintic.
• Indole, an analog with CH in place of nitrogen in position 3.
• Purine, an analog with two additional nitrogen atoms in the six-membered ring.
• Simple aromatic rings
• Triclabendazole, most common drug against liver flukes

References