Facile Approach to Diverse Diarylmethane Scaffolds via DBU-Catalyzed 1,6-Addition Reaction: Discovery of an Antibacterial Agent

ACS Omega, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 15, 2025

Herein, a DBU-catalyzed 1,6-Michael addition of para-quinone methides (p-QMs) under mild reaction conditions with high efficiency (turnover number up to 103) and good excellent yields is reported. The transformation proceeds smoothly range nucleophiles, providing diverse diarylmethane scaffolds efficiency. Mechanistic studies revealed that DBU an proton acceptor donor can promote the methanol p-QMs. A preliminary investigation was also conducted antibacterial properties products.

Language: Английский

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1,6-Conjugate hydrogenation of para-quinone methides to phenol-containing diaryl- and triarylmethanes under atmospheric pressure catalyzed by a metal–ligand bifunctional iridium catalyst

Journal of Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 115812 - 115812

Published: Oct. 1, 2024

Language: Английский

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Directed Palladium‐Catalyzed pseudo‐Anomeric C−H Functionalization of Glycal‐Type Substrates: Access to Unsymmetrical gem‐Diarylmethyl C‐Glycosides

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(6), P. 820 - 825

Published: Feb. 22, 2023

Pd(II)-Catalyzed, bidentate directing group (BDG)-assisted C(sp2)−H functionalization of C2-amido glycals onto the anomeric position is described as a contemporary method for construction various unsymmetrical gem-diarylmethyl C-glycosides. Thanks to amidoquinoline-type group, insertion diverse para-quinone methides (p-QMs) pseudo-anomeric glycal substrates were executed in moderate good yields. Further final product can be successfully demonstrated by known palladium-catalyzed cross-coupling reactions. As service our authors and readers, this journal provides supporting information supplied authors. Such materials are peer reviewed may re-organized online delivery, but not copy-edited or typeset. Technical support issues arising from (other than missing files) should addressed Please note: The publisher responsible content functionality any Any queries content) directed corresponding author article.

Language: Английский

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Multicomponent Synthesis of Biologically Relevant S‐Diarylmethane Dithiocarbamates Using p‐Quinone Methides

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1549 - 1554

Published: March 16, 2022

Abstract A metal and base‐free, operationally simple, scalable multicomponent approach towards the synthesis of S ‐diarylmethane dithiocarbamates is reported. range structurally electronically diverse p ‐quinone methides are shown to react with a variety amines, carbon disulfide furnish corresponding in good excellent yields under mild conditions. Furthermore, ‐QMs embedded aliphatic substituents well accommodated. Importantly, these readily accessible compounds demonstrated promising anti‐proliferative activity low micromolar ranges lung adenocarcinoma cells, reiterating importance developed methodology. magnified image

Language: Английский

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TEMPO-Mediated Synthesis of Indolyl/Imidazo[1,2-a]pyridinyl-Substituted para-Quinone Methides from Butylated Hydroxytoluene

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(23), P. 17090 - 17100

Published: Nov. 11, 2021

A series of indolyl or imidazo[1,2-a]pyridinyl-substituted para-quinone methides (p-QMs) is prepared by a metal-free, TEMPO-mediated cross-dehydrogenative coupling butylated hydroxytoluene (BHT) with indoles imidazo[1,2-a]pyridines in good to high yields. Broad substrate scope respect and imidazo[1,2-a]pyridines, functional group tolerance, acid/base-free conditions are advantageous feature the developed protocol. The method was amenable for scale-up on gram scale. Based control experiments, reaction mechanism proposed describe this transformation.

Language: Английский

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An Efficient Approach to Access 2,2‐Diarylanilines via Visible‐Light‐Promoted Decarboxylative Cross‐Coupling Reactions

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(9), P. 2342 - 2346

Published: July 24, 2021

Abstract A straightforward protocol for the visible‐light‐promoted decarboxylative 1,6‐conjugate addition of N ‐aryl glycines to para ‐quinone methides under transition‐metal‐free conditions is disclosed. This method provides scalable and efficient access 2,2‐diarylanilines with biological pharmacologic potential in good excellent yields (39 examples, up 97% yield). The synthetic utility this work has been illustrated synthesis 3‐substituted indoline.

Language: Английский

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Enantioselective 1,6‐Conjugate Addition of Dialkyl α‐Diazo Methylphosphonate to para‐Quinone Methides

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(21), P. 4856 - 4861

Published: Aug. 28, 2021

Abstract An asymmetric 1,6‐conjugate addition reaction of dialkyl diazomethylphosphonates to para ‐quinone methides promoted by phase‐transfer catalysis has been developed. A series chiral diarylmethylated were accessed with up 85% yields and 99% ee enantioselectivities. The resulting products further transformed into bioactive compounds, namely, a dihydrocinnoline phosphonate α‐aminophosphonate, bearing diarylmethine stereogenic centers. magnified image

Language: Английский

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Phosphine-Catalyzed γ′-Carbon 1,6-Conjugate Addition of α-Succinimide Substituted Allenoates with Para-Quinone Methides: Synthesis of 4-Diarylmethylated 3,4-Disubstituted Maleimides

Molecules, Journal Year: 2024, Volume and Issue: 29(11), P. 2593 - 2593

Published: May 31, 2024

In this paper, an interesting γ′-carbon 1,6-conjugate addition for phosphine-catalyzed α-succinimide substituted allenoates has been disclosed. A wide array of substrates was found to participate in the reaction, resulting production diverse 4-diarylmethylated 3,4-disubstituted maleimides with satisfactory outstanding yields. Furthermore, a plausible mechanism reaction proposed by investigators.

Language: Английский

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B/Pd Synergistic Catalysis for the Decarboxylative Allylation of 2-(2-Azaaryl)acetic Acids

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

Published: Sept. 13, 2024

We describe an allylation reaction between 2-(2-azaaryl)acetic acids and allylic electrophiles catalyzed synergistically by a dual system consisting of borinic acid Pd complex under mild conditions. The decarboxylative proceeds via boron-bound enamine intermediate, which then interacts with π-allylpalladium intermediate from the electrophile. High yields diallylation products highlight method's efficiency. Intriguingly, when using 2-(2-pyridyl)acetic C3 substituent on pyridyl ring, exclusively monoallylation products.

Language: Английский

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1,6-Addition of indolizines to para-quinone methides with indium(III) chloride as catalyst

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 125, P. 154622 - 154622

Published: June 29, 2023

Language: Английский

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