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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.Descrevemos neste trabalho a ação de ácido trifluoroacético, ácido trifluorometanossulfônico e cloreto de alumínio sobre aril azidas orto-substituídas para formar indóis, azepinas e arilaminas com bons rendimentos. As azidas protonadas perdem nitrogênio para formar íons arilnitrênios intermediários que sofrem N-substituição aromática intramolecular. A decomposição ácida de aril azidas é comparada com resultados de termólise tomados da literatura

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