Sie befinden Sich nicht im Netzwerk der Universität Paderborn. Der Zugriff auf elektronische Ressourcen ist gegebenenfalls nur via VPN oder Shibboleth (DFN-AAI) möglich. mehr Informationen...
Ergebnis 26 von 983

Details

Autor(en) / Beteiligte
Titel
Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine
Ist Teil von
  • Angewandte Chemie (International ed.), 2015-09, Vol.54 (40), p.11809-11812
Auflage
International ed. in English
Ort / Verlag
Weinheim: WILEY-VCH Verlag
Erscheinungsjahr
2015
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
  • Treatment of o‐nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)–H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxy, and amino groups were tolerated. From β,β‐disubstituted o‐nitrostyrenes, 2,3‐disubstituted indoles were formed by a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterize the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine. Mild and efficient treatment of o‐nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)–H amination process. A concise synthesis of a marketed drug (rizatriptan) and a formal total synthesis of aspidospermidine featuring this novel N‐heterocyclization process are reported.
Sprache
Englisch
Identifikatoren
ISSN: 1433-7851
eISSN: 1521-3773
DOI: 10.1002/anie.201505713
Titel-ID: cdi_proquest_miscellaneous_1753537915

Weiterführende Literatur

Empfehlungen zum selben Thema automatisch vorgeschlagen von bX