l‐(2‐Aminophenyl)pyrrole (I) and l‐[2‐(aminomethyl)]phenylpyrrole hydrochloride (III) undergo cyclization reactions with aldehydes and ketones to form 4,5‐dihydropyrrolo[l,2‐a]‐ quinoxalines and 5,6‐dihydropyrrolo[l,2‐a][l,4]benzodiazepines, respectively. It was also found that the use of the free base of compounds corresponding to III do not cyclize directly but lead instead to the intermediate Schiff bases which are subsequently cyclized to the desired benzodiazepines by treatment with hydrochloric acid.

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The reaction of 2‐aminopyridine, o‐phthaldehydic acid and potassium cyanide gave pyrido[2′,1′:2,3]imidazo[4,5‐c]isoquinolin‐5(6H)‐one, which upon treatment with propargylbromide, yielded both O and N alkylated products. 2‐Aminopyridine, o‐phthaldehyde and potassium cyanide gave 1‐cyano‐2‐(2‐pyridyl)isoindole which rearranged in acid to give the previously unreported parent pyrido[2′,1′:2,3]imidazo[4,5‐c]isoquinole. Structures were confirmed using uv, ir, nmr and x‐ray spectroscopy.