Transition-Metal-Free, Intermolecular Azidoheteroarylation of Alkenes: Efficient Access to β-Azidoalkylated Quinoxalinones and Preliminary Antifungal Evaluation Against Magnaporthe grisea

Du, Yiming; Chen, Yue; Liu, Yunling; Qin, Weiwei; Li, Zhaodong

doi:10.1055/s-0040-1707514

Cited by 16 publications

(2 citation statements)

References 8 publications

(14 reference statements)

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“…In 2020, Qin et al [ 52 ] published a cascade azidoalkylation reaction with a free radical mechanism ( Scheme 19 ). This three-component reaction used PhI(OAc) 2 as an oxidant to provide a valuable series of β-azidoalkylated quinoxalinones by coupling olefins, quinoxalin-2(1 H )-ones, and TMSN 3 .…”

Section: Direct C–h Functionalization Of Quinoxalin-2(1 H ...mentioning

confidence: 99%

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

Yang

Wang

et al. 2023

Molecules

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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.

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Section: Direct C–h Functionalization Of Quinoxalin-2(1 H ...mentioning

confidence: 99%

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

Yang

Wang

et al. 2023

Molecules

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“…In 2020, Li and coworkers [38] developed a three component strategy for the reaction of quinoxalin‐2(1 H )‐ones, TMSN 3 and alkenes under transition‐metal‐free conditions by employing PhI(OAc) 2 as oxidants (Scheme 21). 41 examples were offered from 32 % to 98 % yields.…”

Section: Nitrogen‐centered Radical Speciesmentioning

confidence: 99%

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

Wang,

Ji,

et al. 2023

Eur J Org Chem

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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.The red front was covered by Figure 1.

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Rhodium‐Catalyzed Dual C−H Activation for Regioselective Triple Annulation of Enaminones: Access to Polycyclic Naphthopyran Derivatives

et al. 2023

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Rh‐catalyzed C−H activation of arenes for oxidative annulations with alkynes stands out as a protocol for polycyclic scaffolds. This perspective drives us to disclose herein a rhodium catalyzed regioselective triple annulation of enaminones with hydroxyl‐alkynoates via double C−H functionalization for polycyclic naphtho‐pyran scaffolds. Secondary coordination of OH in alkynoate dictated the regioselectivity. Initial lactonization occurred chemoselectively on to enamine part via carbo rhodation followed by reductive elimination. This protocol was scalable and has shown high functionality tolerance. KIE studies were done to get insight in to the mechanism, and some downstream transformations were achieved to show the synthetic potential of the method.

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Transition-Metal-Free, Intermolecular Azidoheteroarylation of Alkenes: Efficient Access to β-Azidoalkylated Quinoxalinones and Preliminary Antifungal Evaluation Against Magnaporthe grisea

Cited by 16 publications

References 8 publications

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

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

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

Rhodium‐Catalyzed Dual C−H Activation for Regioselective Triple Annulation of Enaminones: Access to Polycyclic Naphthopyran Derivatives

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