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Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo‐Diaza‐Cope Rearrangement

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Gerosa,  Gabriela Guillermina
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Schwengers,  Sebastian Armin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Maji,  Rajat
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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De,  Chandra Kanta
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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anie.202005798.pdf
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Citation

Gerosa, G. G., Schwengers, S. A., Maji, R., De, C. K., & List, B. (2020). Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo‐Diaza‐Cope Rearrangement. Angewandte Chemie International Edition, 59(46), 20485-20488. doi:10.1002/anie.202005798.


Cite as: http://hdl.handle.net/21.11116/0000-0007-3111-E
Abstract
We disclose a new Brønsted acid promoted quinoline synthesis, proceeding via homo‐diaza‐Cope rearrangement of N‐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.