Synthesis of Benzoxazinones via DIPEA-Promoted Condensation of Benzoxazoles with α-Keto Acids

被引:0
|
作者
Yang, Zhiyong [1 ]
Yan, Jiaqi [1 ]
Guo, Jing [1 ]
Chen, Ping [1 ]
机构
[1] Hunan Univ Arts & Sci, Furong Coll, Changde, Hunan Province, Peoples R China
来源
CHEMISTRYSELECT | 2024年 / 9卷 / 30期
关键词
3-Aryl-2H-Benzo[b][1,4]oxazin-2-ones; Benzoxazoles; alpha-Keto acids; DIPEA; Metal-free; DERIVATIVES; INHIBITORS; ARYLATION;
D O I
10.1002/slct.202401876
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and environmental protocol for the synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones under mild benign conditions has been developed. This facile one-pot approach to 3-aryl-2H-benzo[b][1,4]oxazin-2-ones from commercially available benzoxazoles and alpha-keto acids which only promoted by DIPEA. The protocol exhibits a wide range of applicability in terms of benzoxazoles and alpha-keto acids. Notably, the 2-aryl benzothiazoles can be produced under the similar reaction conditions.
引用
收藏
页数:4
相关论文
共 50 条
  • [41] Synthesis of β-substituted α-amino acids via Lewis acid promoted enantioselective radical conjugate additions
    He, LW
    Srikanth, GSC
    Castle, SL
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (20): : 8140 - 8147
  • [42] Nickel Promoted Condensation of Acetamide and Benzonitrile for the Synthesis of an Imidoylamidine (N-NacNac) via Stable Imidoylamide Intermediate
    Calona, Celeo R. Guifarro
    Filatov, Alexander S.
    Pedro, Brian
    Rybak-Akimova, Elena V.
    ORGANOMETALLICS, 2019, 38 (12) : 2512 - 2522
  • [43] Synthesis of selenated γ-lactones via Oxone-promoted selenylation and cyclization of alkenoic acids with diselenides
    Kim, Kyeong Seop
    Maeng, Nayeon
    Kim, Dae Young
    RESULTS IN CHEMISTRY, 2022, 4
  • [44] A novel base-promoted synthesis of β-indolylketones via a three-component condensation under ultrasonic irradiation
    Shen, ZL
    Ji, SJ
    Wang, SY
    Zeng, XF
    TETRAHEDRON, 2005, 61 (44) : 10552 - 10558
  • [45] Iodine-promoted efficient synthesis of diheteroaryl thioethers via the integration of iodination/condensation/cyclization/dehydration sequences
    Xue, Wei-Jian
    Li, Hong-zheng
    Zheng, Kai-lu
    Wu, An-xin
    TETRAHEDRON LETTERS, 2014, 55 (40) : 5544 - 5547
  • [46] ASYMMETRIC SYNTHESIS OF ALPHA-AMINO-ACIDS VIA A STEREOSELECTIVE 4-COMPONENT CONDENSATION
    SEMPLE, JE
    WANG, PC
    LYSENKO, Z
    JOULLIE, MM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (SEP): : 124 - 124
  • [47] Solid phase synthesis of substituted coumarin-3-carboxylic acids via the Knoevenagel condensation
    Watson, BT
    Christiansen, GE
    TETRAHEDRON LETTERS, 1998, 39 (33) : 6087 - 6090
  • [48] Direct synthesis of fluorene-based spirolactones through a BF3-promoted spiroannulation of α-keto acids and o-alkynylbiaryls
    Song, Qingting
    Zhang, Zhen
    Xie, Xiaoyu
    Ding, Guang-Zhu
    Li, Pinhua
    Wang, Lei
    Miao, Tao
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (02) : 363 - 368
  • [49] SYNTHESIS OF GAMMA-KETO CARBOXYLIC-ACIDS FROM GAMMA-KETO-ALPHA-CHLORO CARBOXYLIC-ACIDS VIA CARBONYLATION DECARBOXYLATION REACTIONS CATALYZED BY A PALLADIUM SYSTEM
    CAVINATO, G
    TONIOLO, L
    JOURNAL OF MOLECULAR CATALYSIS, 1993, 78 (02): : 121 - 129
  • [50] Scalable and Chemoselective Synthesis of γ-Keto Esters and Acids via Pd-Catalyzed Carbonylation of Cyclic β-Chloro Enones
    Kaplan, Justin M.
    Hruszkewycz, Damian P.
    Strambeanu, Iulia I.
    Nunn, Christopher J.
    VanGelder, Kelsey F.
    Dunn, Anna L.
    Wozniak, Derek I.
    Dobereiner, Graham E.
    Leitch, David C.
    ORGANOMETALLICS, 2019, 38 (01) : 85 - 96