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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Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF3-α-Amino Carboxylates

Vorobyeva, Daria V.; Petropavlovskikh, Dmitry A.; Godovikov, Ivan A.; Dolgushin, Fedor M.; Osipov, Sergey N.

Molecules (Basel, Switzerland), 12/2022, Volume: 27, Issue: 23

Journal Article

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.

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Vorobyeva, Daria V. | Petropavlovskikh, Dmitry A. | Godovikov, Ivan A. | Dolgushin, Fedor M. | Osipov, Sergey N.

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