Benzimidazole undergoes reversible dearomatisation with 2,2′-iminodibenzoyl chloride to yield a triazahexacyclic compound (8a). Analogous cyclisations succeeded with 5,6-dimethylbenzimidazole and 4-quinazolone, and with acyclic amidines. Imidazole itself yields the diazocine derivative (19).
A. Banerji, J. C. Cass and A. R. Katritzky, J. Chem. Soc., Perkin Trans. 1, 1977, 1162 DOI: 10.1039/P19770001162
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