Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles.

A synthetic method for the efficient assembly of benzo[c]carbazole derivatives that relies on silica gel-activated benzoic acid-mediated cycloaromatization of 1H-indol-2-yl propargyl benzoates under atmospheric conditions is described. Robust with a variety of substitution patterns tolerated, the reaction provides a one-step strategy to construct a member of the N-heterocycles family in good to excellent yields. A tentative mechanism is proposed in which the cycloaromatization process is thought to involve a Brønsted acid-mediated formal 1,3-acyloxy migration/6π-electrocyclization pathway.