Allylic Acetal as 3C Synthon in Rh(III)-Catalyzed Divergent C–H Activation/[4 + 3] Annulation: Easy Access to Benzodiazepines

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 2, 2025

A concise synthesis of benzodiazepines via Rh(III) catalyzed C-H activation/ [4 + 3] annulation easily available 1-arylpyrazolidinones with allylic acetal has been developed. The was employed as a novel 3C synthon in this transformation. Benzodiazepines were built under mild reaction conditions high efficiency and chemoselectivity. atom-economy accessible substrates reveal potential application.

Language: Английский

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N-Iodosuccinimide-Promoted Synthesis of Indolo[3,2-c]quinolizines via Cascade Intramolecular C–N Bond Formation/Aromatization with 3-(1H-Indol-3-yl)-2-(pyridin-2-yl)propanoates

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

Published: April 10, 2025

An NIS-promoted cascade of intramolecular C-N bond formation/aromatization with 3-(1H-indol-3-yl)-2-(pyridin-2-yl)propanoates is described for synthesizing a polycyclic indole skeleton, indolo[3,2-c]quinolizine, as well 1,9-dihydropyrazolo[4',3':5,6]pyrido[2,3-b]indole. The advantages this protocol include accessible starting materials, mild conditions, simple operation, and good yields. Indolo[3,2-c]quinolizines exhibited fluorescence properties effective staining live cells, targeting lysosomes mitochondria. Additionally, the products showed significant antiproliferative activity against tumor cells in MTT assay.

Language: Английский

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Interrupted Barton–Zard Reaction/Friedel–Crafts Alkylation Telescoped Reaction for the Synthesis of Pyrrolo[3,4‐b]indole Cores

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

Published: May 26, 2025

Abstract A dearomatization reaction between electron‐deficient indoles and α,α‐diaryl‐substituted methyleneisocyanides, followed by in situ Friedel–Crafts alkylation, is described. In a telescoped mediated Brønsted base the first step acid second step, aryl‐substituted pyrrolo[3,4‐b]indole cores are generally obtained moderate‐to‐good yields with high diastereoselectivity. The tolerates wide range of 3‐nitroindoles aryl nucleophiles; however, substrate scope isocyanide derivatives limited. developed methodology offers modular approach for synthesis multi‐substituted polycyclic cores.

Language: Английский

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Organocatalytic enantioselective (4+3) cyclization for the synthesis of spiro-fused heterocyclic compounds containing isoindolinone, oxepine and indole moieties

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(70), P. 9400 - 9403

Published: Jan. 1, 2024

A refined strategy has been developed to control the regioselective asymmetric (4+3) cyclization of α-(3-isoindolinonyl) propargylic alcohols with 2-indolylmethanols, utilizing chiral phosphoric acid catalysis. This innovative organocatalytic yields spiro isoindolinone-oxepine-fused indoles featuring a spiro-quaternary stereocenter in high and enantioselectivities, facilitated by solvent 1,1-dichloro-1-fluoroethane additive hexafluoroisopropanol. Additionally, photophysical properties product 3k are examined, revealing bright fluorescence both solution solid state.

Language: Английский

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