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

被引：6
作者：
Wan, Shuocheng [1 ]
Wang, Jie [1 ]
Huo, Congde [1 ]
机构：
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Gansu Int Sci & Technol Cooperat, Base Water Retent Chem Funct Mat, Lanzhou 730070, Gansu, Peoples R China
来源：
TETRAHEDRON LETTERS | 2021年 / 78卷
基金：
中国国家自然科学基金;
关键词：
Aerobic; Amination; Oxidation; Copper; 3-Aminoquinoxalinones; 3,4-Dihydroquinoxalin-2(1H)-ones; QUINOXALINE DERIVATIVES; BOND FORMATION; INHIBITORS; DESIGN;
D O I：
10.1016/j.tetlet.2021.153271
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper catalyzed aerobic sp(3) C-H amination of 3,4-dihydroquinoxalin-2(1H)-ones is developed. This protocol provides a concise method to access 3-aminoquinoxalinone derivatives with good functional-group tolerances, utilizing primary and secondary aliphatic amines as nitrogen sources under mild and simple reaction conditions. It provides a practical approach to the synthesis of pharmaceutical active 3-aminoquinoxalinones. (C) 2021 Elsevier Ltd. All rights reserved.
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页数：4
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共 30 条
  • [1] Perspectives on 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives
    Achari, B
    Mandal, SB
    Dutta, PK
    Chowdhury, C
    [J]. SYNLETT, 2004, (14) : 2449 - 2467
  • [2] Visible-light-induced C(sp3)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1H)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions
    Akula, Pavan Sudheer
    Hong, Bor-Cherng
    Lee, Gene-Hsiang
    [J]. RSC ADVANCES, 2018, 8 (35): : 19580 - 19584
  • [3] Structural insights into binding of inhibitors to soluble epoxide hydrolase gained by fragment screening and X-ray crystallography
    Amano, Yasushi
    Yamaguchi, Tomohiko
    Tanabe, Eiki
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (08) : 2427 - 2434
  • [4] [Anonymous], [No title captured], Patent No. [US 20050070527A1, 20050070527]
  • [5] REACTIONS OF 19-ETHOXYCARBONYL-19-DEMETHYLVINCADIFFORMINE - SYNTHESIS OF 19-ETHOXYCARBONYL-19-DEMETHYLAPOVINCAMINE
    BELATTAR, A
    SAXTON, JE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (13): : 1583 - 1585
  • [6] Novel synthesis of 3,4-dihydro-5-bromo[1,4]oxazin-2-one derivatives, new protease inhibitor scaffold
    Bihel, F
    Kraus, JL
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (05) : 793 - 799
  • [7] ALKALOID STUDIES .46. ALKALOIDS OF ASPIDOSPERMA OBSCURINERVIUM AZEMBUJA - NEW CLASS OF HEPTACYCLIC INDOLE ALKALOIDS
    BROWN, KS
    DJERASSI, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (12) : 2451 - &
  • [8] Chakravarty P., 2009, WO, Patent No. [WO 2009045382A1, 2009045382, 2009045382 A1]
  • [9] Iron-Catalyzed C(sp3)-C(sp3) Bond Formation in 3,4-Dihydro-1,4-benzoxazin-2-ones
    Dong, Jie
    Min, Wenjian
    Li, Haitao
    Quan, Zhengjun
    Yang, Caixia
    Huo, Congde
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (22) : 3940 - 3944
  • [10] Design, synthesis and structure-activity relationship of novel quinoxaline derivatives as cancer chemopreventive agent by inhibition of tyrosine kinase receptor
    Galar, Shadia A.
    Abdelsamie, Ahmed S.
    Soliman, Salwa M.
    Mortier, Jeremie
    Wolber, Gerhard
    Ali, Mamdouh M.
    Tokuda, Harukuni
    Suzuki, Nobutaka
    Lida, Akira
    Ramadan, Raghda A.
    El Diwani, Hotta I.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 69 : 115 - 124
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