RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
Synfacts 2009(1): 0021-0021
DOI: 10.1055/s-0028-1087460
DOI: 10.1055/s-0028-1087460
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Highly Substituted Indoles via an Intramolecular Heck Cyclization
L. El Kaim*, M. Gizzi, L. Grimaud*
École Nationale Supérieure de Techniques Avancées, Paris, France
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. Dezember 2008 (online)
Significance
A combined multi-component Ugi-Smiles reaction followed by a Heck cyclization for the synthesis of substituted indole derivatives in good to high yield has been developed. Thus the Ugi-Smiles reaction of o-iodophenols, aldehydes, isocyanides and allyl amines gives highly functionalized aniline derivatives which, under Pd-catalyzed cyclization followed by isomerization, yield the highly substituted indoles. Furthermore, hydroxy pyrimidines were found to give indolopyrimidines by the corresponding reactions. Both reactions were successfully carried out in one-pot, with the addition of trifluoroacetic acid (0.2-0.3 equiv to affect the hydrolysis of the remaining isocyanide) before Heck cyclization.