Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of <i>N</i>-Ethoxycarbonyl-<i>N</i>-Propargylanilines
oleh: Antonio Arcadi, Andrea Calcaterra, Giancarlo Fabrizi, Andrea Fochetti, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Vincenzo Marsicano, Giulia Mazzoccanti, Andrea Serraiocco
| Format: | Article |
|---|---|
| Diterbitkan: | MDPI AG 2021-06-01 |
Deskripsi
An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of <i>N</i>-ethoxycarbonyl protected-<i>N</i>-propargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-<i>endo</i> cyclization product in good to high yields. In the presence of <i>N</i>-ethoxycarbonyl-<i>N</i>-propargyl-<i>meta-</i>substituted anilines, the regiodivergent cyclization at the <i>ortho</i>-/<i>para</i>-position is achieved by the means of catalyst fine tuning.