Three‐Component Reactions of Quinoxalin‐2(1H)‐ones: Recent Advances

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Sept. 11, 2023

Abstract The multicomponent reactions of quinoxalin‐2(1 H )‐ones has attracted considerable interest due to their significant biological and chemical activities. very recent advances (from 2021 the beginning 2023) on radical three‐component cascade reaction )‐one derivatives at C3 position were summarized in this mini‐review. According kind types involved, some representative examples detailed mechanism have been categorized discussed. red front was covered by Figure 1.

Language: Английский

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Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2758 - 2763

Published: April 24, 2024

Abstract Herein, we present a (NH 4 ) 2 S O 8 mediated difunctionalization reaction of aryl alkenes with quinoxalinones and P(O)SH compounds. This method enables the synthesis various phosphorothioate‐containing quinoxalin‐2(1 H )‐one derivatives (46 examples) in 37–79% yields. The is compatible range functional groups easily adaptable to large‐scale synthesis. Preliminary studies suggest involvement phosphorothioate radicals these transformations.

Language: Английский

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Photoredox-Catalyzed Three-Component Amidoheteroarylation of Unactivated Alkenes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4113 - 4118

Published: May 30, 2023

A photoredox-catalyzed 1,2-amidoheteroarylation of unactivated alkenes with O-acyl hydroxylamine derivatives and heterocycles is presented. range heterocycles, including quinoxaline-2(1H)-ones, azauracils, chromones, quinolones, are capable for this process, allowing the direct synthesis valuable heteroarylethylamine derivatives. Structurally diverse reaction substrates, drug-based scaffolds, were successfully applied, demonstrating practicality method.

Language: Английский

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Synthesis of Alkyl Fluorides and Fluorinated Unnatural Amino Acids via Photochemical Decarboxylation of α-Fluorinated Carboxylic Acids

Organic Letters, Journal Year: 2023, Volume and Issue: 25(3), P. 483 - 487

Published: Jan. 18, 2023

Leveraging α-fluoroalkyl or fluorobenzyl radicals to introduce fluorinated motifs allows for the rapid preparation of fluorine-containing building blocks. Herein, we report generation from readily available α-fluorocarboxylic acids under mild reaction conditions and their utilization in Giese-type addition on Michael acceptors dehydroamino acids, resulting mono- difluorinated adducts unnatural amino acids.

Language: Английский

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Recent Developments in Direct C–H Functionalization of Quinoxalin-2(1H)-Ones via Multi-Component Tandem Reactions

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2513 - 2513

Published: March 9, 2023

The direct C-H multifunctionalization of quinoxalin-2(1H)-ones via multicomponent reactions has attracted considerable interest due to their diverse biological activities and chemical profile. This review will focus on recent achievements. It mainly covers reaction methods for the simultaneous introduction C-C bonds C-RF/C/O/N/Cl/S/D into mechanisms. Meanwhile, future developments multi-component are envisaged, such as construction C-B/SI/P/F/I/SE through reactions; fused ring macrocyclic compounds; asymmetric synthesis; green chemistry; bionic structures other fields. aim is enrich at C3 position, which have rich applications in materials chemistry pharmaceutical pharmacology.

Language: Английский

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Visible-Light-Initiated Difunctionalization of Quinoxalin-2(1H)-ones with Acyloxy Nitroso Compounds

Organic Letters, Journal Year: 2022, Volume and Issue: 24(39), P. 7118 - 7122

Published: Sept. 25, 2022

Herein, a photoinitiated radical relay reaction of quinoxalin-2(1H)-ones, with acyloxy nitroso compounds as source radicals, is described. Although the C-H functionalization quinoxalin-2(1H)-ones has been investigated, its difunctionalization, simultaneous construction C-C and N-N bonds directly via reaction, rarely reported. Moreover, obtained products underwent sequential reactions to access C7-NO2 under mild conditions.

Language: Английский

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Trichloromethyl‐Radical‐Initiated Three‐Component Reaction of Alkenes with CHCl₃ and Quinoxalinones

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(5), P. 687 - 692

Published: Feb. 8, 2023

Abstract An iron(II)‐catalyzed three‐component reaction was developed for the construction of trichloromethylated 3‐benzylquinoxalin‐2(1 H )‐ones. This conducted through trichloromethylation alkenes with quinoxalin‐2(1 )‐ones using commercially available chloroform as trichloromethyl radical source, which provided a convenient approach toward magnified image

Language: Английский

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Visible‐Light‐Driven Multicomponent Radical Cascade Versatile Alkylation of Quinoxalinones Enabled by Electron Donor Acceptor Complex in Water

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(7), P. 1020 - 1026

Published: March 10, 2023

Abstract An operationally simple aqueous phase three‐component photochemical strategy for the alkylation of quinoxalin‐2(1 H )‐ones with diethyl α ‐bromomalonate and unactivated alkenes in absence both photoredox catalysts additive has been developed. This reaction is driven by activity electron donor‐acceptor (EDA) complexes formed ‐bromomalonate. Irradiation visible light triggered single‐electron transfer (SET) from to ‐bromomalonate, inducing formation corresponding alkyl radical subsequent tandem reaction. It provides an efficient way construct alkylated quinoxalinones small molecules. magnified image

Language: Английский

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Atom Transfer Radical Addition Reactions of Quinoxalin-2(1H)-ones with CBr₄ and Styrenes Using Mes-Acr-MeClO₄ Photocatalyst

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1784 - 1796

Published: Jan. 12, 2024

The atom transfer radical addition (ATRA) reaction is defined as a method for introducing halogenated compounds into alkenes via mechanism. In this study, we present an ATRA approach achieving regioselective functionalization of quinoxalin-2(1H)-ones by activating C–Br bonds CBr4 and subsequent trihaloalkyl-carbofunctionalization styrenes employing the 9-mesityl-10-methylacridinium perchlorate (Fukuzumi) photocatalyst under 3W blue LED (450–470 nm) irradiation. This three-component cascade process demonstrates remarkable efficiency in synthesis 1-methyl-3-(3,3,3-tribromo-1-(4-chlorophenyl)propyl)quinoxalin-2(1H)-one derivatives.

Language: Английский

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Metal- and additive-free β-C(sp2)-H decarboxylative alkylsulfonylation of enamides from phenyliodine(III) dicarboxylates and sulfur dioxide

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(63), P. 8212 - 8215

Published: Jan. 1, 2024

A green process for the direct C(sp 2 )–H decarboxylative alkylsulfonylation of enamides under metal- and additive-free conditions is reported.

Language: Английский

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