Functionalized 4-Aminoquinolines by Rearrangement of Pyrazole N-Heterocyclic Carbenes

Functionalized 4-Aminoquinolines by Rearrangement of Pyrazole N-Heterocyclic Carbenes

Thermal decarboxylation of 1‐phenylpyrazolium‐3‐carboxylates from the mesomeric betaine class of substances leads to pyrazole‐N‐heterocyclic carbenes, which immediately rearrange to multiply substituted 4‐aminoquinolines (see scheme). These species are of interest for the synthesis of heterocycles a...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-04, Vol.49 (15), p.2790-2793
Hauptverfasser: Schmidt, Andreas, Münster, Niels, Dreger, Andrij
Format: Artikel
Sprache:eng
Schlagworte:
Aminoquinolines - chemical synthesis
Aminoquinolines - chemistry
Antimalarials - chemistry
carbenes
Catalysis
Coordination Complexes - chemistry
heterocycles
Heterocyclic Compounds - chemistry
Methane - analogs & derivatives
Methane - chemistry
Pyrazoles - chemistry
rearrangements
synthetic methods
zwitterions
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Beschreibung
Zusammenfassung:Thermal decarboxylation of 1‐phenylpyrazolium‐3‐carboxylates from the mesomeric betaine class of substances leads to pyrazole‐N‐heterocyclic carbenes, which immediately rearrange to multiply substituted 4‐aminoquinolines (see scheme). These species are of interest for the synthesis of heterocycles and pharmacologically active compounds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200905436