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Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor
O. Ghashghaei, M. Pedrola, F. Seghetti, VV. Martin, R. Zavarce, M. Babiak, J. Novacek, F. Hartung, KM. Rolfes, T. Haarmann-Stemmann, R. Lavilla
Language English Country Germany
Document type Journal Article, Research Support, Non-U.S. Gov't
- MeSH
- Aldehydes chemistry MeSH
- Cyclization MeSH
- Indoles chemistry MeSH
- Humans MeSH
- Ligands MeSH
- Molecular Structure MeSH
- Receptors, Aryl Hydrocarbon chemistry MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
The participation of reactants undergoing a polarity inversion along a multicomponent reaction allows the continuation of the transformation with productive domino processes. Thus, indole aldehydes in Groebke-Blackburn-Bienaymé reactions lead to an initial adduct which spontaneously triggers a series of events leading to the discovery of novel reaction pathways together with direct access to a variety of linked, fused, and bridged polyheterocyclic scaffolds. Indole 3- and 4-carbaldehydes with suitable isocyanides and aminoazines afford fused adducts through oxidative Pictet-Spengler processes, whereas indole 2-carbaldehyde yields linked indolocarbazoles under mild conditions, and a bridged macrocycle at high temperature. These novel structures are potent activators of the human aryl hydrocarbon receptor signaling pathway.
CEITEC Masaryk University University Campus Bohunice 62500 Brno Czech Republic
IUF Leibniz Research Institute for Environmental Medicine 40225 Düsseldorf Germany
References provided by Crossref.org
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