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

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

An acid-functionalized ionic liquid (IL)-catalyzed cascade decarboxylative cyclization of 2-arylanilines with α-oxocarboxylic acids was developed. This approach offered a sustainable and practical pathway to afford a library of quinoxalines in water under ambient conditions. This protocol tolerated various kinds of functional groups and could be easily scaled-up. The developed method featured a recyclable catalytic system, environmentally friendly reaction conditions, simple operation, and a practical workup procedure, which represented the potential to streamline quinoxaline synthesis in industry. A possible mechanism involving a dual activation strategy to promote both decarboxylation and cyclization processes was proposed.

Bifunctional acidic ionic liquid-catalyzed decarboxylative cascade synthesis of quinoxalines in water under ambient conditions

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 of C–C bonds and C–RF/C/O/N/Cl/S/D bonds into quinoxalin-2(1H)-ones and their reaction mechanisms. Meanwhile, future developments of multi-component reactions of quinoxalin-2(1H)-ones are envisaged, such as the simultaneous construction of C–C and C–B/SI/P/F/I/SE bonds through multi-component reactions; the construction of fused ring and macrocyclic compounds; asymmetric synthesis; green chemistry; bionic structures and other fields. The aim is to enrich the methods for the reaction of quinoxalin-2(1H)-ones at the C3 position, which have rich applications in materials chemistry and pharmaceutical pharmacology.

https://www.mdpi.com/1420-3049/28/6/2513/pdf?version=1678372837

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

Development of a Metal- and Oxidant-Free Enzyme–Photocatalyst Hybrid System for Highly Efficient C-3 Acylation Reactions of Indoles with Aldehydes

Herein, we present a (NH4)2S2O8 mediated difunctionalization reaction of aryl alkenes with quinoxalinones and P(O)SH compounds. This method enables the synthesis of various phosphorothioate‐containing quinoxalin‐2(1H)‐one derivatives (46 examples) in 37‐79% yields. The reaction is compatible with a range of functional groups and is easily adaptable to large‐scale synthesis. Preliminary studies suggest the involvement of phosphorothioate radicals in these transformations.

Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

An attractive and convenient strategy for the direct acylation/annulation of indoles has been developed using Pd(0) as an efficient catalyst. The main feature of this protocol is the use of acyl chlorides as the acylating agents with the primary amine as the directing group. A variety of indolo[1,2-a]quinoxalines were readily obtained in reasonable efficiency and satisfactory yields with good functional group tolerance. Based on control experiments, a tentative catalytic mechanism was proposed.

Palladium-catalyzed sequential acylation/annulation of indoles with acyl chlorides using primary amine as the directing group

An efficient transition metal-free difunctionalization of alkenes in water for the green preparation of sulfone compounds

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Palladium-catalyzed sequential acylation/annulation of indoles with acyl chlorides using primary amine as the directing group

An efficient transition metal-free difunctionalization of alkenes in water for the green preparation of sulfone compounds