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-Npropargylanilines 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-metasubstituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning.
Synthesis of 4-substituted-1,2-dihydroquinolines by means of gold-catalyzed intramolecular hydroarylation reaction of n-ethoxycarbonyl-n-propargylanilines / Arcadi, A.; Calcaterra, A.; Fabrizi, G.; Fochetti, A.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Marsicano, V.; Mazzoccanti, G.; Serraiocco, A.. - In: MOLECULES. - ISSN 1420-3049. - 26:11(2021), p. 3366. [10.3390/molecules26113366]