Intramolecular carbocupration of N-aryl-ynamides: a modular indole synthesis
Wafa Gati1, François Couty, Taoufik Boubaker
1Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines , 45, avenue des Etats-Unis, 78035 Versailles Cedex, France, Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Département de Chimie, Faculté des Sciences de Monastir, Université de Monastir , avenue de l'environnement, 5019 Monastir, Tunisia, and Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université Libre de Bruxelles , Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium.
Abstract:
A modular indole synthesis based on an intramolecular 5-endo-dig carbocupration starting from readily available N-aryl-ynamides is reported. A variety of ynamides are converted to indoles in moderate to good yields and with varying substitution pattern on the indole ring. This further extends the synthetic utility of ynamides in organic synthesis and provides additional insights on the use of intramolecular carbometalation reactions.
More Related Videos
Related Concept Videos
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Preparation of Nitriles
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Nomenclature of Aryl and Heterocyclic Amines
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...


