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Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF3-α-Amino Carboxylates |
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| Authors: | Daria V. Vorobyeva Dmitry A. Petropavlovskikh Ivan A. Godovikov Fedor M. Dolgushin Sergey N. Osipov |
| Affiliation: | 1.A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28/1 Vavilova Str., 119334 Moscow, Russia;2.N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky pr. 31, 119071 Moscow, Russia;3.Plekhanov Russian University of Economics, 36, Stremyanny Per., 117997 Moscow, Russia |
| Abstract: | A convenient pathway to a new series of α-CF3-substituted α-amino acid derivatives bearing pharmacophore isoquinolone core in their backbone has been developed. The method is based on [4+2]-annulation of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing α-amino carboxylates under Rh(III)-catalysis. The target annulation products can be easily transformed into valuable isoquinoline derivatives via a successive aromatization/cross-coupling operation. |
| Keywords: | acetylenes amino acids C-H activation annulation catalysis isoquinolones |