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

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: Английский

Facile Synthesis of Functionalized Quinolinones in Greener Reaction Medium and Their Photophysical Properties

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A facile and green chemical approach was successfully developed to construct functionalized quinolinones utilizing substituted alcohols, alkyl acetoacetate, α-bromo ketones. Various bearing either electron-rich or electron-deficient groups at different positions were synthesized in moderate good yields under mild reaction conditions. The plausible mechanistic pathway for this transformation is supported by experimental evidence control experiments. This simple synthesizing could open new avenues discovering novel biological pharmaceutical compounds. use of affordable nickel catalysts, conditions, operational simplicity, high atom economy are attractive features method. Furthermore, the synthetic efficiency has been demonstrated through gram-scale Our research also provides valuable insights into photophysical properties derivatives. Notably, compound 6n exhibited highest Stokes shift (216 nm) DCM solvent. compounds 5d 6j showed positive solvatochromism, displaying a stronger emission as solvent polarity increased. Additionally, displayed aggregation-induced (AIE) DMSO : water mixture, making it suitable security ink, highlighting its potential applications various fields.

Language: Английский

Cobalt‐Catalyzed Synthesis of Functionalized Nordazepams and Benzimidazoquinazolines and Their Photophysical Properties

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract An efficient and environmentally friendly one‐pot sequential synthesis of functionalized nordazepam a benzimidazoquinazoline analogue is reported, utilizing cobalt as the metal catalyst. The reaction proceeds via either α ‐alkenylation or dehydrogenative sp 3 C−H functionalization pathway. This transformation includes mild conditions, operational simplicity, good functional group tolerance. Additionally, this method suitable for gram‐scale compounds. Furthermore, synthetic utility, photophysical properties real‐life application synthesized derivatives were explored.

Language: Английский