Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines

Calcaterra, Andrea; Fabrizi, Giancarlo; Andrea Fochetti; Goggiamani, Antonella; Iazzetti, Antonia; Marrone, Federico; Marsicano, Vincenzo; Mazzoccanti, Giulia; Serraiocco, Andrea; Arcadi, Antonio

doi:10.3390/molecules26113366

Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines

Author(s)

Calcaterra, Andrea

Fabrizi, Giancarlo

Andrea Fochetti

Goggiamani, Antonella

Iazzetti, Antonia

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Date Issued

2021

Type

article

Volume

26

Issue

11

Start Page

3366

DOI

10.3390/molecules26113366

Journal

MOLECULES

Abstract

An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-meta-substituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning.

Handle

http://hdl.handle.net/2067/51033