Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines

Abstract

We describe in this paper the action of trifluoroacetic acid, trifluoromethanesulfonic acid and aluminum chloride upon ortho-substituted aryl azides to form indoles, azepines and arylamines in good yields. The protonated azides lose nitrogen to form arylnitrenium ion intermediates which undergo intramolecular aromatic N-substitution. The acid decomposition of aryl azides is compared with reported thermolyses.

Keywords

• nitrenium ion
• aryl azides
• indoles
• azepines