Copper-Catalyzed Multi-Component Reactions: Synthesis of Nitrogen-Containing Polycyclic Compounds

ISBN-13: 9783642154720 / Angielski / Twarda / 2011 / 104 str.

Yusuke Ohta

Opis

As the concept of Green Chemistry becomes ever more important, the findings presented in this book may provide efficient and atom-economical approaches to the diversity-oriented synthesis of bioactive compounds containing a complex structure.

Spis treści

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-β-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

Blurb

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.