Direct C‐2 arylation of quinoxaline with arylhydrazine salts as arylation reagents

Wang, Xing; Wang, Bing; Jing, Miao; Chen, Yi; Zhu, Guoqi; Zhang, Jiquan; Wang, Jianta; Wang, Haibo; Tang, Lei

doi:10.1002/jhet.4465

Cited by 3 publications

(1 citation statement)

References 44 publications

(31 reference statements)

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“…Based on the literature reports, control experiment and CV analysis, − the pathway for the electrochemical arylation of C(sp 2 )–H with aryl tetrafluoroborate diazonium salt are proposed and explained in Scheme . First, the phenyl tetrafluoroborate diazonium salt ( 2a ) is initially reduced at the surface of the cathode to generate the corresponding phenyl diazo radical ( A ).…”

Section: Results and Discussionmentioning

confidence: 99%

Electrochemical C–H Arylation of Quinazolinone with Aryl Tetrafluoroborate Diazonium Salts in Aqueous Solution of Ionic Liquids

Ji,

Zhang,

Zhao

et al. 2023

ACS Sustainable Chem. Eng.

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A process for the electrochemical direct C−H arylation of quinazolinones and aryl tetrafluoroborate diazonium salts with ionic liquid [EMIM]BF 4 (1-ethyl-3-methylimidazolium tetrafluoroborate):H 2 O (2:1) as electrolyte was developed for the synthesis of 2-arylquinazolinones, and a series of 2-arylquinazolinones were synthesized with moderate to good yields. This method was applied for the synthesis of a key intermediate of an IKK β inhibitor CU160 and a quinazolinone alkaloid 2-(1H-indol-3-yl) quinazolin-4(3H)-one. The mild and green synthesis scheme provides an effective alternative to the traditional synthesis of 2-arylquinazolinone.

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Section: Results and Discussionmentioning

confidence: 99%

Electrochemical C–H Arylation of Quinazolinone with Aryl Tetrafluoroborate Diazonium Salts in Aqueous Solution of Ionic Liquids

Ji,

Zhang,

Zhao

et al. 2023

ACS Sustainable Chem. Eng.

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Synthesis of N,N‐Disubstituted Hydrazines by Electrocatalytic Addition of Hydrazines to α,β‐Unsaturated Carbonyl Compounds

Xu,

Zhang,

et al. 2024

Adv Synth Catal

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A strategy for the synthesis of N,N‐disubstituted hydrazines via the electrocatalytic addition of hydrazine to α,β‐unsaturated carbonyl compounds is reported. The reaction was carried out under constant current electrolytic conditions in an undivided cell. Using this methodology, various N,N‐disubstituted hydrazines are prepared with 57‐94% yields in 40 min. By adding cyclohexanone and acetic acid to the reaction mixture of N,N‐disubstituted hydrazines and heating for 2 h, a "one‐pot" synthesis of N‐substituted indoles has also been developed. Furthermore, based on cyclic voltammetry and controlled experiments, a plausible mechanism involving the radical pathway is proposed.

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Mn-Mediated Direct Regioselective C–H Trifluoromethylation of Imidazopyridines and Quinoxalines

Firuz,

Rajai-Daryasarei,

Rominger

et al. 2023

J. Org. Chem.

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A simple and highly efficient strategy has been developed for direct C–H trifluoromethylation at C-3 of imidazopyridines and C-8 of quinoxalines with readily available Langlois reagent through KMnO4/AcOH system. This protocol showed broad substrate scope and afforded moderate-to-excellent yields of both products. It is the first report that the functionalization of quinoxalines occurred regioselectively at the C-8 position of quinoxalines. Mechanistic studies revealed that reaction proceeded via radical pathway.

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Direct C‐2 arylation of quinoxaline with arylhydrazine salts as arylation reagents

Cited by 3 publications

References 44 publications

Electrochemical C–H Arylation of Quinazolinone with Aryl Tetrafluoroborate Diazonium Salts in Aqueous Solution of Ionic Liquids

Electrochemical C–H Arylation of Quinazolinone with Aryl Tetrafluoroborate Diazonium Salts in Aqueous Solution of Ionic Liquids

Synthesis of N,N‐Disubstituted Hydrazines by Electrocatalytic Addition of Hydrazines to α,β‐Unsaturated Carbonyl Compounds

Mn-Mediated Direct Regioselective C–H Trifluoromethylation of Imidazopyridines and Quinoxalines

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