DECOMPOSITION ACIDO-CATALYSEE D'AZIDES TERTIAIRES BENZOCYCLOBUTENIQUES. NOUVELLE METHODE DE SYNTHESE DU NOYAU INDOLIQUE PAR EXTENSION DU CYCLE

Article abstract of DOI:10.1016/S0040-4020(01)96432-4

Treatment of benzocyclobutenols substituted on the functional carbon by the HN3/BF3-Et2O reagent allows the synthesis to the corresponding tertiary azides.The latter by acid-catalysed breakdown, lead to 2-substituted indoles.A similar result is obtained by treating directly the alcohols with hydrazoic acid and concentrated sulfuric acid.This new route to indole nucleus is also extended to the synthesis of policyclic indoles.