Synthesis of Indazole Fused 2-Benzazepines with Polarity-Dependent Fluorescence Based on Formal [4 + 3] Annulation of 3-Aryl-1H-indazoles with Cyclopropenones

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

Published: April 3, 2025

The effective assembly of benzazepine skeletons in a sustainable and atom-economical fashion remains challenging goal modern organic synthesis. Presented herein is novel synthesis indazole fused 2-benzazepine derivatives based on formal [4 + 3] annulation 3-aryl-1H-indazoles with cyclopropenones. formation products proceeds through Ir(III)-catalyzed aryl C-H bond metalation cyclopropenone ring-opening leading to acylation, followed by an intramolecular N-nucleophilic conjugated addition. By using this method, number valuable were effectively generated. This protocol addresses the challenges constructing medium-sized rings cascade C-H/C-C activation C-C/C-N formation. Moreover, photophysical properties thus obtained also evaluated. It turned out that all compounds tested showed solvent polarity-dependent fluorescence features, which could be potentially applied for revealing polarity their immediate environments.

Language: Английский

Synthesis of branched and linear aryl allylic alcohols: C H bond allylation of 2-aryl-3H-indoles with vinyl cyclic carbonates

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 147, P. 155225 - 155225

Published: Aug. 4, 2024

Language: Английский