Sunlight Induced and Recyclable g-C3N4 Catalyzed C-H Sulfenylation of Quinoxalin-2(1H)-Ones

Peng, Sha; Liu, Jiao; Yang, Lihua; Xie, Long‐Yong

doi:10.3390/molecules27155044

Cited by 9 publications

(6 citation statements)

References 89 publications

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“…At the same time, an electron from the CB is transferred to O2 (air) to form O2 •− , which has been confirmed by EPR analysis using 5,5-dimethyl-1-pyrroline (DMPO) as a spin trapping agent. Next, O2 In the same year, Xie et al reported a sunlight-induced and g-C3N4-catalysed sulfenylation reaction of quinoxalin-2(1H)-ones under air conditions (Scheme 7) [44]. The reactions of this method offer a very attractive and practical way to selectively obtain a wide variety of 3-sulphated quinolin-2(1H)-ones in good to excellent yields.…”

Section: Scheme 3 G-c3n4-catalyzed Divergent Heterogeneous Reactionmentioning

confidence: 99%

“…In the same year, Xie et al reported a sunlight-induced and g-C 3 N 4 -catalysed sulfenylation reaction of quinoxalin-2(1 H )-ones under air conditions ( Scheme 7 ) [ 44 ]. The reactions of this method offer a very attractive and practical way to selectively obtain a wide variety of 3-sulphated quinolin-2(1 H )-ones in good to excellent yields.…”

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

confidence: 99%

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Recent Developments in Direct C–H Functionalization of Quinoxalin-2(1H)-Ones via Heterogeneous Catalysis Reactions

Yang

Wang

et al. 2023

Molecules

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In recent years, Web of Science has published nearly one hundred reports per year on quinoxalin-2(1H)-ones, which have attracted great interest due to their wide applications in pharmaceutical and materials fields, especially in recyclable heterogeneous catalytic reactions for direct C–H functionalisation. This review summarises for the first time the methods and reaction mechanisms of heterogeneous catalytic reactions of quinoxalin-2(1H)-ones, including six major types of heterogeneous catalysts involved. The heterogeneous reactions of quinoxalin-2(1H)-ones are summarised by classifying different types of catalytic materials (graphitic phase carbon nitride, MOF, COF, ion exchange resin, piezoelectric materials, and microsphere catalysis). In addition, this review discusses the future development of heterogeneous catalytic reactions of quinoxalin-2(1H)-ones, including the construction of C-B/Si/P/RF/X/Se bonds by heterogeneous catalytic reactions, the enrichment of heterogeneous catalysts such as metal oxides, graphene-based composites, doped metal nanoparticles, and molecular sieve-based porous materials, asymmetric synthesis, and other areas. The aim of this review is to contribute to the development of green and sustainable heterogeneous reaction methods for quinoxalin-2(1H)-ones with applications in materials chemistry and pharmacology.

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Section: Scheme 3 G-c3n4-catalyzed Divergent Heterogeneous Reactionmentioning

confidence: 99%

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 Heterogeneous Catalysis Reactions

Yang

Wang

et al. 2023

Molecules

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“…[16,17] Chemical advances in total synthesis, synthetic methods, chemical biology, and drug discovery have all focused on pyrazines, which have a six-membered aromatic structure with two nitrogen atoms arranged in a 1,4-orientation embedded within a carbon framework and exhibit unique chemical reactivity profiles. [18,19] Many biological studies of pyrazine and hybrid compounds have shown their therapeutic efficacy concerning human health and sickness after looking at the ideal cavity and structural core of pyrazine nitrogen. [20,21] Some important pyrazines (amiloride, bortezomib, pyrazinamide) and many more are shown in Figure 2 as being on the 2019 WHO's Model List of Essential Medicines.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Quinoline‐Pyrazine Based Carboxamides: Leukemic Cancer Active Ugi Adducts

Piludiya,

Kamdar,

Khedkar

et al. 2024

ChemistrySelect

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The design and synthesis of new chemical entities (NCEs) with suitable physicochemical properties are playing a key role in medicinal research areas. Hence, we have designed and synthesized the 10 diverse scaffolds by rightly selecting the quinoline and pyrazine to articulate carboxamide derivatives in a single‐step process with maximum conversation in a shorter time through diverse studies of Ugi multi‐component reaction. Molecular docking studies against FMS‐like tyrosine kinase‐3 (FLT3) provided well‐clustered solutions for the binding modes of these molecules and shed light on the key structural features governing the binding affinity. Two carboxamides derivatives with 3,4,5‐trimethoxy, and chloro substituents showed comparable potency in Leukemia cell lines and medium efficacy in Breast and Melanoma cancer. These results suggest that pyrazine and quinoline‐based carboxamides may be prominent as new anti‐cancer agents in chemotherapy. Additionally, in silico analysis was employed to predict the comprehensive physicochemical ADME profile (absorption, distribution, metabolism, and excretion) of the carboxamide derivatives which was proven drug‐like properties.

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“…However, to our knowledge, the carbamoyl-radical-triggered cascade cyclization reaction of N3-alkenyl-tethered quinazolinones to afford amide-containing quinazolinones has never been reported. With our continuing interest in radical chemistry [ 64 , 65 , 66 , 67 , 68 ], herein, we report a metal-free protocol for the synthesis of amide-substituted polycyclic quinazolinones through the cascade radical carbamoylation/cyclization reaction of N3-alkenyl-tethered quinazolinones with oxamic acids as a readily available carbamoyl radical source ( Scheme 1 b).…”

Section: Introductionmentioning

confidence: 99%

Persulfate-Promoted Carbamoylation/Cyclization of Alkenes: Synthesis of Amide-Containing Quinazolinones

Tang,

Zhao,

Lin

et al. 2024

Molecules

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The incorporation of amide groups into biologically active molecules has been proven to be an efficient strategy for drug design and discovery. In this study, we present a simple and practical method for the synthesis of amide-containing quinazolin-4(3H)-ones under transition-metal-free conditions. This is achieved through a carbamoyl-radical-triggered cascade cyclization of N3-alkenyl-tethered quinazolinones. Notably, the carbamoyl radical is generated in situ from the oxidative decarboxylative process of oxamic acids in the presence of (NH4)2S2O8.

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Sunlight Induced and Recyclable g-C3N4 Catalyzed C-H Sulfenylation of Quinoxalin-2(1H)-Ones

Cited by 9 publications

References 89 publications

Recent Developments in Direct C–H Functionalization of Quinoxalin-2(1H)-Ones via Heterogeneous Catalysis Reactions

Recent Developments in Direct C–H Functionalization of Quinoxalin-2(1H)-Ones via Heterogeneous Catalysis Reactions

Design and Synthesis of Quinoline‐Pyrazine Based Carboxamides: Leukemic Cancer Active Ugi Adducts

Persulfate-Promoted Carbamoylation/Cyclization of Alkenes: Synthesis of Amide-Containing Quinazolinones

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