Expanding Diversity of Fused Steroid-Quinoline Hybrids by Sequential Amination/Annulation/Aromatization Reactions

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 7, 2025

Viable alternative approaches to a variety of ring A and D-fused steroid-quinoline hybrids, along with A, D-fused, and/or A-fused, side chain-substituted steroid-bis-quinolines were explored by means sequential amination/annulation/aromatization reactions suitable ketosteroids 2-acyl-substituted anilines. Key factors directing the chemoselective behavior polyfunctionalized substrates investigated. Remarkably, use TMSOTf as an promoter/catalyst enabled direct synthesis desired avoiding protection/deprotection steps conventional procedures when starting contained labile functional groups.

Язык: Английский

TMSOTf/TfOH-Promoted [4 + 2] Annulation of Ynamides with 2-Aminoarylnitriles To Construct 2,4-Diaminoquinolines

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 9, 2025

An effective strategy to synthesize 2,4-diaminoquinoline compounds has been efficaciously developed via a TMSOTf/TfOH-promoted [4 + 2] annulation of ynamides with 2-aminoarylnitriles. Compared the reported transition-metal catalysts, this metal-free promotion system presented remarkable advancement, enabling facile and regiospecific assembly frameworks wide functional group compatibility moderate excellent yields.

Язык: Английский

Copper-Catalyzed [2,3]-Sigmatropic Rearrangement of Azide–Ynamides via Selenium Ylides

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 23, 2024

A copper-catalyzed [2,3]-sigmatropic rearrangement of azide-ynamides via selenium ylides is disclosed, which leads to the practical and divergent synthesis a variety tricyclic heterocycles bearing quaternary carbon stereocenter in generally moderate excellent yields. Significantly, this method represents first ylide based on alkynes an unprecedented α-imino copper carbenes.

Язык: Английский