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The Synthesis of Hydroquinolines from Nitroaldehydes and Ketones by Hydrogenation Sequences and Condensations

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: https://doi.org/10.1002/chem.202500462

Abstract in another language

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.

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: WOS:001457452400001
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Operando-Analytics of Electrochemical Energy Storage > Chair Operando-Analytics of Electrochemical Energy Storage - Univ.-Prof. Dr. Thomas Lunkenbein
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Operando-Analytics of Electrochemical Energy Storage
Result of work at the UBT: Yes
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 12 Jun 2025 06:58
Last Modified: 04 Jul 2025 11:31
URI: https://eref.uni-bayreuth.de/id/eprint/93647