Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines |
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| Authors: | Antonio Arcadi Andrea Calcaterra Giancarlo Fabrizi Andrea Fochetti Antonella Goggiamani Antonia Iazzetti Federico Marrone Vincenzo Marsicano Giulia Mazzoccanti Andrea Serraiocco |
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| Affiliation: | 1.Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi di L’Aquila, 67100 Coppito, Italy; (A.A.); (V.M.);2.Dipartimento di Chimica e Tecnologie del Farmaco, Dipartimento di Eccellenza 2018–2022, Sapienza Università di Roma, 00185 Rome, Italy; (A.C.); (G.F.); (A.F.); (F.M.); (G.M.); (A.S.) |
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| 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. |
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| Keywords: | gold catalysis intramolecular hydroarylation 1 2-dihydroquinolines |
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