Synthesis of 2-Substituted Indoles through Cyclization and Demethylation of 2-Alkynyldimethylanilines by Ethanol
Résumé
Herein, we demonstrated that 2-alkynyldimethylamines easily cyclize in EtOH according to a 5-endo-dig annulation into 2-substituted indoles without the aid of any additive or any metal catalyst to activate the triple bond. Thus, a variety of functionalized 2-styrylindoles, 2-arylindoles, 2-alkynylindoles, and 2-alkylindoles were prepared in high to excellent yields according to an environmentally friendly protocol. The mechanism has been explored to better understand this eco-friendly access to 2-substituted indoles and DFT computations rationalized the role of the solvent in this N-annulation/dealkylation process.
Domaines
Chimie organique
Origine : Fichiers produits par l'(les) auteur(s)
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