Copper catalyzed aerobic oxidative amination of 3,4-dihydroquinoxalin-2(1H)-ones

Wan, Shuocheng; Wang, Jie; Huo, Congde

doi:10.1016/j.tetlet.2021.153271

Cited by 6 publications

(3 citation statements)

References 26 publications

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“…[13] The laboratory of Huo extended its research in this field with its report on the amination of 3,4-dihydroquinoxalin-2ones catalyzed by Cu(II) (Scheme 7). [14] In this case, the N-4unprotected 3,4-dihydroquinoxalin-2-ones 1 reacted with different primary and secondary amines 14 in the presence of Cu(OAc) 2 under an air atmosphere. However, the formed aminated 3,4-dihydroquinoxalin-2-one 15 was reoxidized to form the expected aminated quinoxalin-2-one 16.…”

Section: Nucleophilic Functionalizationsmentioning

confidence: 99%

Catalytic Nucleophilic and Electrophilic Functionalization of Dihydroquinoxalin‐2‐ones

et al. 2023

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Financial support from grant PID2020‐116944GB funded by MCIN/AEI/10.13039/501100011033 and by “ERDF A way of making Europe” and CIAICO/2021/147 funded by Conselleria d'Innovació, Universitat, Ciència i Societat Digital is acknowledged. J.R.‐B. thanks the Ministerio de Ciencia, Innovación y Universidades for a FPU predoctoral contract (FPU17/00688). C.V. thanks the RyC contract (RYC‐2016‐20187) funded by MCIN/AEI/10.13039/501100011033 and by “European Union NextGeneration EU/PRTR”. Access to NMR, MS, and X‐ray facilities from the Servei Central de Suport a la Investigació Experimental (SCSIE)‐UV is also acknowledged.

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Section: Nucleophilic Functionalizationsmentioning

confidence: 99%

Catalytic Nucleophilic and Electrophilic Functionalization of Dihydroquinoxalin‐2‐ones

et al. 2023

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“…Purification by column chromatography on silica gel (eluents: EtOAc/hexane = 2.5/7.5); white solid (53 mg, 76% yield); mp = 148–150 °C (Lit., 156–158 °C); 1 H NMR (400 MHz, CDCl 3 ): δ 11.56 (s, 1H), 7.57 (d, J = 8.0 Hz, 1H), 7.28–7.24 (m, 1H), 7.22–7.20 (m, 2H), 6.35 (t, J = 5.4 Hz, 1H), 3.57 (q, J = 6.8 Hz, 2H), 1.78 (sext, J = 7.3 Hz, 2H), 1.07 (t, J = 7.4 Hz, 3H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ): δ 152.9, 149.5, 134.2, 126.9, 125.4, 124.5, 123.9, 115.3, 42.7, 22.4, 11.6; HRMS (ESI) m / z : [M + H] + Calcd for C 11 H 14 N 3 O, 204.1131; found, 204.1130.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…Purification by column chromatography on silica gel (eluents: EtOAc/hexane = 2.5/7.5); white solid (53 mg, 62% yield); mp = 128–130 °C (Lit., 130–132 °C); 1 H NMR (400 MHz, CDCl 3 ): δ 11.30 (s, 1H), 7.61–7.59 (m, 1H), 7.46 (d, J = 7.2 Hz, 2H), 7.40 (t, J = 7.2 Hz, 2H), 7.36–7.32 (m, 1H), 7.30–7.25 (m, 1H), 7.24–7.18 (m, 2H), 6.61 (t, J = 5.6 Hz, 1H), 4.80 (d, J = 5.6 Hz, 2H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ): δ 152.7, 149.2, 138.2, 134.0, 128.7, 128.1, 127.6, 127.1, 125.6, 124.6, 124.2, 115.3, 45.0; HRMS (ESI) m / z : [M + H] + Calcd for C 15 H 14 N 3 O, 252.1131; found, 252.1135.…”

Section: Experimental Sectionmentioning

confidence: 99%

Selectfluor-Mediated Regioselective C-3 Alkoxylation, Amination, Sulfenylation, and Selenylation of Quinoxalin-2(1H)-ones

et al. 2023

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A Selectfluor-promoted oxidative coupling of quinoxalin-2(1H)-ones with alcohols, amines, thiols, and selenols leading to the formation of C–O, C–N, C–S, and C–Se bonds has been developed. The protocol provided good to excellent (53–95%) yields of a wide range of quinoxalin-2(1H)-ones decorated with alkoxy, alkylamino, alkylthio, and arylselenyl groups at the C3-position under metal- and photocatalyst-free conditions. The reaction is believed to proceed through a radical pathway. A broad substrate scope including bioactive molecules, mild reaction conditions, readily available coupling partners, high yields, scalability, step-economy, and metal- and photocatalyst-free conditions are the highlighting features of the method. The synthetic utility of the developed protocol was demonstrated by gram-scale synthesis, C3-alkoxylation of quinoxaline-2(1H)-one with natural alcohols, and synthesis of aldose reductase (ALR2) inhibitor and histamine-4 receptor antagonist in good yields.

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Visible‐light‐induced Catalyzed Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Azoles Using Carbon Nitride

Xie

Wang

et al. 2022

Asian J Org Chem

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An efficient visible‐light‐induced catalyzed dehydrogenation coupling of quinoxalin‐2(1H)‐ones with azoles was developed, a protocol that did not require prefunctionalization of the substrates and produced hydrogen (H2). Meanwhile, this reaction proceeded without the addition of other metal and oxidant and provided a broad range of 3‐aminoquinoxalin‐2(1H)‐ones in medium to good yield. Furthermore, this protocol provided advantages of easy and simple operation, high chemoselectivity, and a recyclable catalyst. A preliminary mechanistic investigation revealed that the reaction involved a radical process.

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Copper catalyzed aerobic oxidative amination of 3,4-dihydroquinoxalin-2(1H)-ones

Cited by 6 publications

References 26 publications

Catalytic Nucleophilic and Electrophilic Functionalization of Dihydroquinoxalin‐2‐ones

Catalytic Nucleophilic and Electrophilic Functionalization of Dihydroquinoxalin‐2‐ones

Selectfluor-Mediated Regioselective C-3 Alkoxylation, Amination, Sulfenylation, and Selenylation of Quinoxalin-2(1H)-ones

Visible‐light‐induced Catalyzed Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Azoles Using Carbon Nitride

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