Selective 2,3′‐Homodimerization of Indoles Using Mechanochemistry: a Convenient Synthesis 2,3′‐Biindoles

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(14)

Published: April 1, 2025

Abstract 2,3‐biindole (or 2,3‐bisindole) is an important structural feature found in many biologically active synthetic and natural products. Though excellent methods have been reported to achieve selective 2,3′homodimerization of indole produce compounds, most them need strong co‐oxidants other additives enable the reactions. In recent times, mechanochemistry picking up as a promising sustainable, environmentally‐benign tool modern organic chemistry. Because, not only presents fair deal avoid use environmentally hazardous, unsafe, expensive large quantities solvents (waste reduction), it also accelerate reactions even new chemical transformations. We herein report such greener, atom‐economical, solvent‐free, oxidant‐free Pd‐catalyzed two indolyl groups furnish compounds environment‐friendly fashion using Liquid Assisted Grinding (LAG) mechanochemical process.

Language: Английский

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Ethanol-assisted mechanochemical asymmetric cross-dehydrogenative coupling reaction with recoverable chiral amine/NaCl for accessing chiral α-alkyl α-glycine derivatives

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(11), P. 6570 - 6577

Published: Jan. 1, 2024

Ethanol-assisted grinding effectively facilitated aerobic asymmetric cross-dehydrogenative coupling of glycine esters/amides with ketones/aldehydes, deploying reusable chiral amine/NaCl for rapid synthesis α-alkyl α-glycine derivatives.

Language: Английский

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Mechanochemical C−H Arylation and Alkylation of Indoles Using 3 d Transition Metal and Zero‐Valent Magnesium

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(26)

Published: Jan. 31, 2024

Although the 3 d transition-metal catalyzed C-H functionalization have been extensively employed to promote formation of valuable carbon-carbon bonds, persistent problems, including use sensitive Grignard reagents and rigorous operations (solvent-drying, inert gas protection, metal pre-activation RMgX addition rate control), still leave great room for further development sustainable methodologies. Herein, we report a mechanochemical technology toward in-situ preparation highly organomagnesium reagents, thus building two general catalytic platforms that enables regioselective arylation alkylation indoles with wide variety halides (including those containing post transformable functionalities heteroaromatic rings). This strategy also brings unique reactivity high step-economy in producing functionalized N-free indole products.

Language: Английский

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Synthesis of bioactive evodiamine and rutaecarpine analogues under ball milling conditions

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(13), P. 2620 - 2629

Published: Jan. 1, 2024

Mechanochemical reactions achieved by processes such as milling and grinding are promising alternatives to traditional solution-based chemistry. This approach not only eliminates the need for large amounts of solvents, thereby reducing waste generation, but also finds applications in chemical materials synthesis. The focus this study is on synthesis quinazolinone derivatives ball milling, particular evodiamine rutaecarpine analogues. These compounds interest due their diverse bioactivities, including potential anticancer properties. examines carried out under conditions, emphasizing efficiency terms shorter reaction times reduced environmental impact compared conventional methods. analogues resulted yields 63-78% 22-61%, respectively. In addition, these were tested cytotoxic activity, exhibited an IC

Language: Английский

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Mechanochemical Bromination of Naphthalene Catalyzed by Zeolites: From Small Scale to Continuous Synthesis

Chemistry - Methods, Journal Year: 2022, Volume and Issue: 2(12)

Published: July 12, 2022

Abstract Catalyzed reactions of organic substrates that operate continuously by extrusion techniques are rare. In this study, we developed a mechanochemical bromination unactivated naphthalene ( 1 ) with 1,3‐dibromo‐5,5‐dimethylhydantoin DBDMH ), catalyzed zeolites in ball mill. The use enabled the atom economy reaction to be superior compared other brominating agents evaluated. Among tested, FAU‐type zeolite demonstrated high catalytic activity and recyclability. success route on small scale development continuous twin‐screw extrusion.

Language: Английский

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