Hypervalent iodine mediated C-H amination of quinoxalinones with heteroaromatic amines under metal-free conditions

“…Given the above experimental and previous reports, [ 31 ] a plausible reaction mechanism was proposed as shown in Scheme 3. Under the irradiation of a green LED, the ground state 4CzIPN reached the excited state 4CzIPN*.…”

Section: Resultsmentioning

confidence: 86%

Photocatalytic Transition‐Metal‐Free Direct 3‐Acetalation of Quinoxaline‐2(1H)‐ones

Meng

et al. 2022

Chin. J. Chem.

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Comprehensive Summary A general transition‐metal‐free visible‐light‐promoted 3‐acetalation reaction of quinoxaline‐2(1H)‐ones was developed under mild conditions. By employing 1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene (4CzIPN) as an inexpensive photocatalyst, and glyoxylic acid acetal as a radical source, various acetalated quinoxaline‐2(1H)‐ones were constructed in moderate to good yields. Moreover, the versatility of this protocol is highlighted by the successful application in the late‐stage modification of drug molecules and the various functionality transformations. The excellent antitumor activity of the acetalated product demonstrated that this streamlined and sustainable approach could have emerged as a powerful strategy for structural modification in medicinal chemistry.

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“…Quinoxaline-2-ketone derivatives are widely found in bioactive molecules [ 71 , 95 ]. In 2019, the direct C-3 difluoroacetylation of quinoxalinones using ethyl bromodifluoroacetate catalyzed by copper was reported by Zhang’s group ( Scheme 34 ) [ 96 ].…”

Section: Difluoroalkylation–coupling Reactionsmentioning

confidence: 99%

Copper-Catalyzed Difluoroalkylation Reaction

et al. 2022

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Hypervalent iodine mediated C-H amination of quinoxalinones with heteroaromatic amines under metal-free conditions

Cited by 26 publications

References 58 publications

Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles

Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles

Photocatalytic Transition‐Metal‐Free Direct 3‐Acetalation of Quinoxaline‐2(1H)‐ones

Copper-Catalyzed Difluoroalkylation Reaction

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