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URN to cite this document: urn:nbn:de:bvb:703-epub-8981-6
Title data
Bauer, Christof ; Zareh, Fatemeh ; Nüßlein, Lisa ; Frank, Johanna ; Boniface, Maxime ; Lunkenbein, Thomas ; Kempe, Rhett:
The Synthesis of Hydroquinolines from Nitroaldehydes and Ketones by Hydrogenation Sequences and Condensations.
In: Chemistry : a European Journal.
Vol. 31
(2025)
Issue 28
.
- e202500462.
ISSN 1521-3765
DOI der Verlagsversion: https://doi.org/10.1002/chem.202500462
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Project information
| Project title: |
Project's official title Project's id SFB 1585: Strukturierte Funktionsmaterialien für multiplen Transport in nanoskaligen räumlichen Einschränkungen 492723217 Open Access Publizieren No information |
|---|---|
| Project financing: |
Deutsche Forschungsgemeinschaft |
Abstract
Catalytic reaction discovery or methodology development is preferably performed with homogeneous catalysts, but heterogeneous catalysts allow the design of complex multistep syntheses based on their reusability. We introduce here the catalytic synthesis of hydroquinolines starting from nitroaldehydes, ketones and hydrogen. The reaction is complex and proceeds via multiple selective hydrogenation and condensation steps. The nitroaldehyde is selectively hydrogenated forming an aminoaldehyde, followed by a base-catalyzed Friedl & auml;nder synthesis and selective quinoline hydrogenation. The starting materials are inexpensive, simple regarding their structure and diversely available, and the hydroquinoline motif is part of numerous biologically active compounds. A nanostructured earth-abundant metal catalyst mediates our reaction most efficiently.
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