Base-Promoted and Copper(I)-Catalyzed Tandem Cyclization-C(sp²)-N Coupling of Vinyl Malononitriles with Ortho-Nitrochalcones: Access to Acridones and their Fused Derivatives

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

Published: Feb. 28, 2025

An efficient Cs2CO3-promoted and copper(I)-catalyzed double cyclization of ortho-nitrochalcones with vinyl malononitriles for the de novo access to a variety tri- tetra-substituted acridones their fused derivatives value-added CN group has been developed first time. This one-pot operation proceeds through Michael-cyclization-aromatization, followed by regioselective ipso-amination via nucleophilic aromatic substitution (SNAr) reaction, resulting in two C═C bonds C-N bond acridone ring synthesis. economic strategy based on 100% carbon atoms ensures successive formation rings operation, good high yields, wide range substrates, tolerance functionalities. In addition, were converted into several acridines, highlighting synthetic versatility usefulness prepared derivatives.

Language: Английский

Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation Morita-Baylis-Hillman carbonates, organocatalytic dearomatization afforded an array enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34-79% yields with 61-91% ee. With Boc

Language: Английский