Science of Synthesis

Grimmett, M. R., Science of Synthesis, (2002) 12, 600.

As an acid, 1H-benzimidazol-1-amine has a pKa of 12.83.[‌475‌] Such amino groups can be alkylated and acylated by way of their anions,[‌30‌] and they are subject to the usual reactions with carbonyl compounds,[‌158‌,‌476‌–‌478‌] especially as the quaternary salts (but there is often accompanying ring cleavage).[‌479‌] The reactions are base catalyzed, and the Schiff bases formed from 1-alkylbenzimidazol-3-amines also react further to give triazinobenzimidazoles by cyclization at the 2-position.[‌477‌] Oxidation of benzimidazol-1-amines with manganese dioxide or lead(IV) acetate gives either 1,1′-azobenzimidazoles or 3-substituted 1,2,4-benzotriazines. The oxidations involve initial generation of a nitrene.[‌195‌,‌480‌–‌483‌]

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References