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Copper-Catalyzed Multi-Component Reactions
Synthesis of Nitrogen-Containing Polycyclic Compounds
von Yusuke Ohta
Verlag: Springer Berlin Heidelberg
Reihe: Springer Theses
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ISBN: 978-3-642-15473-7
Auflage: 2011
Erschienen am 20.01.2011
Sprache: Englisch
Umfang: 104 Seiten

Preis: 53,49 €

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Inhaltsverzeichnis
Klappentext

Synthesis of Indole Derivatives
Construction of 2-(Aminomethyl)indoles through Copper-Catal¬yzed Domino Three-Component Coupling and Cyclization
Facile Synthesis of 1,2,3,4-Tetrahydro-ß-carbolines by One-Pot Domino Three-Component Indole Formation and Nucleophilic Cyclization
Concise Synthesis of Indole-Fused 1,4-Diazepines through Copper(I)-Catalyzed Domino Three-Component Coupling-Cyclization-N-Arylation under Microwave Irradiation
Synthesis of Isoquinoline Derivatives
Facile Synthesis of 3-(Aminomethyl)isoquinolines by Copper-Catalyzed Domino Four-Component Coupling and Cyclization
Rapid Access to 3-(Aminomethyl)isoquinoline-Fused Polycyclic Compounds by Copper-Catalyzed Four-Component Coupling, Cascade Cyclization, and Oxidation
Conclusions
Acknowledgements



A copper-catalyzed direct synthesis of 2-(aminomethyl)indoles by catalytic domino reaction including multi-component coupling was developed, and is the first example of a three-component indole formation without producing salts as a byproduct. Based on this reaction, a copper-catalyzed synthesis of 3-(aminomethyl)isoquinoline was accomplished which represents an unprecedented isoquinoline synthesis through a four-component coupling reaction. Following these results, extensive application studies using one-pot palladium-, acid-, or base-promoted cyclization revealed that indole- or isoquinoline-fused polycyclic compounds can be readily synthesized through multi-component reactions. As the concept of Green Chemistry becomes ever more important, these findings may provide efficient and atom-economical approaches to the diversity-oriented synthesis of bioactive compounds containing a complex structure. This could lead to development of promising drug leads with structural complexity. The work of this thesis will go on to inspire the synthetic research of many readers.


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