Reaction of Aromatic Azides with Strong Acids: Formation of Fused Nitrogen Heterocycles and Arylamines

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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.

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De Carvalho, M., Sorrilha, A. E. P. M., & Rodrigues, J. A. R. (1999). Reaction of Aromatic Azides with Strong Acids: Formation of Fused Nitrogen Heterocycles and Arylamines. Journal of the Brazilian Chemical Society, 10(5), 415–420. https://doi.org/10.1590/s0103-50531999000500012

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