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

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.

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 Creators:
Gerosa, Gabriela Guillermina1, Author              
Schwengers, Sebastian Armin1, Author              
Maji, Rajat1, Author              
De, Chandra Kanta1, Author              
List, Benjamin1, Author              
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1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: annulation; cyclopropane; DFT calculations; Fischer indolization; quinolines; rearrangements
 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.

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Language(s): eng - English
 Dates: 2020-04-212020-07-042020-11-09
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202005798
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 59 (46) Sequence Number: - Start / End Page: 20485 - 20488 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851