Iodine-Mediated Intramolecular Dehydrogenative Coupling: Synthesis of <i>N</i>‑Alkylindolo[3,2‑<i>c</i>]- and -[2,3‑<i>c</i>]quinoline Iodides

An I₂/TBHP-mediated intramolecular dehydrogenative coupling reaction is developed for the synthesis of a library of medicinally important 5,11-dialkylindolo­[3,2-<i>c</i>]­quinoline salts and 5,7-dimethylindolo­[2,3-<i>c</i>]­quinoline salts. The annulation reaction is followed by aromatization to yield tetracycles in good yield. This protocol is also demonstrated for the synthesis of the naturally occurring isocryptolepine in salt form