Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 46, Pages 20485-20488Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005798
Keywords
annulation; cyclopropane; DFT calculations; Fischer indolization; quinolines; rearrangements
Categories
Funding
- Max-Planck-Institut fur Kohlenforschung
- Horizon 2020 Marie Sklodowska-Curie Postdoctoral Fellowship [897130]
- Max-Planck-Society
- Deutsche Forschungsgemeinschaft (Leibniz Award)
- Deutsche Forschungsgemeinschaft (Cluster of Excellence Ruhr Explores Solvation, RESOLV)
- European Research Council (ERC, European Union's Horizon 2020 research and innovation program C-H Acids for Organic Synthesis, CHAOS Advanced Grant) [694228]
- Projekt DEAL
- Marie Curie Actions (MSCA) [897130] Funding Source: Marie Curie Actions (MSCA)
Ask authors/readers for more resources
We disclose a new Bronsted acid promoted quinoline synthesis, proceeding via homo-diaza-Cope rearrangement ofN-aryl-N '-cyclopropyl hydrazines. Our strategy can be considered a homologation of Fischer's classical indole synthesis and delivers 6-membered N-heterocycles, including previously inaccessible pyridine derivatives. This approach can also be used as a pyridannulation methodology toward constructing polycyclic polyheteroaromatics. A computational analysis has been employed to probe plausible activation modes and to interrogate the role of the catalyst.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available