Über die Verwendung des Rhodanins zu organischen Synthesen V. α‐Indol‐carbonsäure

Gränacher, Ch.; Mahal, A.; Gerö, M.

doi:10.1002/hlca.19240070169

Cited by 9 publications

(1 citation statement)

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“…A solution of ethyl 3-(2-azidophenyl)propenoate 2 (prepared from ethyl propenoate 5) in dichloromethane when treated with triflic acid at 0 °C gave ethyl 1H-indole-2-carboxylate 4 (m.p 124-125 °C) 14 in 38% yield, ethyl E-3-(2-aminophenyl)propenoate (pale yellow needles, m.p. 77-78°C ) 24 5 in 17% yield, ethyl 3-(5-trifluoromethanesulphonate-2-aminophenyl)propenoate 6, mp 85-86 °C, in 5% yield and traces of ethyl 3-(3-trifluoromethanesulphonate-2-aminophenyl) propenoate.…”

Section: Resultsmentioning

confidence: 99%

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

Carvalho¹,

Sorrilha²,

Rodrigues³

1999

J. Braz. Chem. Soc.

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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.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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Section: Resultsmentioning

confidence: 99%