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

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

doi:10.3390/molecules27238488

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

Molecules. 2022 Dec 2;27(23):8488. doi: 10.3390/molecules27238488.

Authors

Daria V Vorobyeva¹, Dmitry A Petropavlovskikh¹, Ivan A Godovikov¹, Fedor M Dolgushin^{2

3}, Sergey N Osipov¹

Affiliations

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: C-H activation; acetylenes; amino acids; annulation; catalysis; isoquinolones.

MeSH terms

Acetylene* / chemistry
Benzamides* / chemistry
Catalysis
Molecular Structure

Substances

Acetylene
Benzamides

Grants and funding

21-13-00328/Russian Science Foundation