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DOI: 10.1055/s-0042-1751546
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Chemical Synthesis and Catalysis in Germany

Synthesis of New Highly Functionalized Quinolines via a Novel FeIII-Catalyzed Domino aza-Michael/Aldol/Aromatization Reaction

Felix Heckmann
a   Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany
,
Mohammad M. Ibrahim
a   Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany
b   Department of Chemistry, Faculty of Science, University of Al al-Bayt, P. O. Box 130040, 25113 Al-Mafraq, Jordan
,
Frank Hampel
a   Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany
,
Svetlana B. Tsogoeva  ∗
a   Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany
› Author AffiliationsWe gratefully acknowledge financial support from the Deutsche Forschungsgemeinschaft (DFG, grant no. TS 87/28-1 for S.B.T.).
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Abstract

We report the development of a straightforward, waste-reducing, environmentally friendly, FeIII-catalyzed domino aza-Michael/aldol/aromatization reaction in the presence of water to access high-value functionalized quinolines by using 2-aminobenzophenones and ethyl buta-2,3-dienoate as starting compounds. The tangible advantages, that is, the utilization of commercially available and/or easily accessible substrates, simplicity, mild reaction conditions, and application of water as a solvent, make this three-step domino process green and highly appealing for the direct construction of a wide variety of highly functionalized quinolines in up to 78% yield.

Key words

domino reactions - Fe catalysis - Lewis acid catalysis - quinoline synthesis - sustainability

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751546.
  • Supporting Information


Publication History

Received: 10 October 2023

Accepted after revision: 11 December 2023

Article published online:
24 January 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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