Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo‐Diaza‐Cope Rearrangement
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.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo‐Diaza‐Cope Rearrangement ; volume:59 ; number:46 ; year:2020 ; pages:20485-20488 ; extent:4
Angewandte Chemie / International edition. International edition ; 59, Heft 46 (2020), 20485-20488 (gesamt 4)
- Creator
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Gerosa, Gabriela Guillermina
Schwengers, Sebastian Armin
Maji, Rajat
De, Chandra Kanta
List, Benjamin
- DOI
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10.1002/anie.202005798
- URN
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urn:nbn:de:101:1-2022061112123414593206
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:32 AM CEST
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Associated
- Gerosa, Gabriela Guillermina
- Schwengers, Sebastian Armin
- Maji, Rajat
- De, Chandra Kanta
- List, Benjamin
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Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides
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Dendritische Diaza-Cope-Umlagerung
Reaktionsübergangszustände der Cope- und Diaza-Cope-Umlagerung
Die Diaza-Cope-Umlagerung : Mechanismus und synthetische Anwendung.
Combining Imine Condensation Chemistry with (3,3) Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures
Combining Imine Condensation Chemistry with (3,3) Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures
Synthesis of Homoallylic Amines via 2-Aza-Cope Rearrangement
Synthesen substituierter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Synthesen pyrimidinhomologer, methanoüberbrückter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Eludicating Heavy‐Atom‐Tunneling Kinetics in the Cope Rearrangement of Semibullvalene
Synthese elongierter Diaza-π-Donor-Cavitäten [Diaza-pi-Donor-Cavitäten]
Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides
Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement
Dendritische Diaza-Cope-Umlagerung
Reaktionsübergangszustände der Cope- und Diaza-Cope-Umlagerung
Die Diaza-Cope-Umlagerung : Mechanismus und synthetische Anwendung.
Combining Imine Condensation Chemistry with (3,3) Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures
Combining Imine Condensation Chemistry with (3,3) Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures
Synthesis of Homoallylic Amines via 2-Aza-Cope Rearrangement
Synthesen substituierter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Synthesen pyrimidinhomologer, methanoüberbrückter Diaza[10]- [Diaza-] und Diaza[14]annulene [Diazaannulene]
Eludicating Heavy‐Atom‐Tunneling Kinetics in the Cope Rearrangement of Semibullvalene
Synthese elongierter Diaza-π-Donor-Cavitäten [Diaza-pi-Donor-Cavitäten]
Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides