An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel-Crafts-type addition to 3-alkylidene indolenium cations

An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel-Crafts-type addition to 3-alkylidene indolenium cations

An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2012-06, Vol.48 (44), p.5431-5433
Hauptverfasser: Yokosaka, Takuya, Nemoto, Tetsuhiro, Hamada, Yasumasa
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cations
Indoles - chemical synthesis
Molecular Structure
Phenols - chemistry
Stereoisomerism
Trifluoroacetic Acid - chemistry
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Zusammenfassung:An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and intramolecular Pictet-Spengler reaction proceeded sequentially, producing tricyclic indole derivatives.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc31699d