Metal-Free Arylation of Ethyl Acetoacetate with Hypervalent Diaryliodonium Salts: An Immediate Access to Diverse 3-Aryl-4(1H)-Quinolones

被引：50
|
作者：
Monastyrskyi, Andrii [1 ]
Namelikonda, Niranjan K. [1 ]
Manetsch, Roman [1 ]
机构：
[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 05期
基金：
美国国家卫生研究院;
关键词：
ONE-POT SYNTHESIS; PALLADIUM-CATALYZED ARYLATION; 2-ARYLACETIC ACID-ESTERS; BETA-KETO-ESTERS; ARYL IODIDES; EFFICIENT; OPTIMIZATION; DERIVATIVES; ANTIMALARIALS; NUCLEOPHILES;
D O I：
10.1021/jo5023958
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A clean arylation protocol of ethyl acetoacetate was developed using hypervalent diaryliodonium salts under mild and metal-free conditions. The scope of the reaction, using symmetric and unsymmetric iodonium salts with varying sterics and electronics, was examined. Further, this method has been applied for the synthesis of antimalarial compound ELQ-300, which is currently in preclinical development.
引用
收藏
页码：2513 / 2520
页数：8
相关论文
共 34 条
  • [21] Nano copper oxide mediated ligand-free C-S cross-coupling and concomitant oxidative aromatization of 4-aryl-3,4-dihydropyrimidin-2(1H)-thione with diaryliodonium salts
    Bhong, Bhagyashree Y.
    Shelke, Amol V.
    Karade, Nandkishor N.
    TETRAHEDRON LETTERS, 2013, 54 (08) : 739 - 743
  • [22] New Substituted 1-Aryl-4,4,6-Trimethyl-3,4-Dihydropyrimidine-2-(1H)Thiones; A Metal-Free and Solvent-Free Synthesis, Characterization, and Lymphoid Tyrosine Phosphatase Inhibition Studies
    Khurshid, Asma
    Saeed, Aamer
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2017, 64 (02) : 224 - 230
  • [23] Base promoted metal-free approach towards synthesis of quinazolin-4 (3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones under microwave irradiation
    Dutta, Apurba
    Sarma, Diganta
    SUSTAINABLE CHEMISTRY AND PHARMACY, 2021, 20
  • [24] Metal-free direct C(sp3)-H functionalization of 2-alkylthiobenzoic acid to access 1,3-benzooxathiin-4-one
    Yang, Ke
    Li, Yi
    Song, Mengjie
    Dai, Shengfei
    Li, Zheng-Yi
    Sun, Xiaoqiang
    CHINESE CHEMICAL LETTERS, 2021, 32 (01) : 146 - 149
  • [25] Metal-Free Oxidative C(sp3)-N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
    Rezaei, Narjes
    Sheikhi, Ehsan
    Ranjbar, Parviz Rashidi
    SYNLETT, 2018, 29 (07) : 912 - 917
  • [26] A Facile Access to Metal-Free Synthesis of 3,4-Dihydropyrimidin-2-(1H)-Ones/Thiones using Acridine Yellow G as a Photo-Induced Electron Transfer Photocatalyst
    Mohamadpour, Farzaneh
    POLYCYCLIC AROMATIC COMPOUNDS, 2024, 44 (01) : 495 - 506
  • [27] Access to 2-Alkyl/Aryl-4-(1H)-Quinolones via Orthogonal "NH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F
    Singh, Shweta
    Nerella, Sharanya
    Pabbaraja, Srihari
    Mehta, Goverdhan
    ORGANIC LETTERS, 2020, 22 (04) : 1575 - 1579
  • [28] A novel direct synthesis of 3-acyl-4-aryldihydroquinolin-2(1H)-ones via metal-free radical tandem cyclization between N-arylcinnamamides and aldehydes
    Mai, Wen-Peng
    Wang, Ji-Tao
    Xiao, Yong-Mei
    Mao, Pu
    Lu, Kui
    TETRAHEDRON, 2015, 71 (42) : 8041 - 8051
  • [29] Reversal of Diastereoselectivity in Reactions of the Trifluoroacetaldehyde Ethyl Hemiacetal with Enamines and Imines: Metal-Free, Complementary anti- and syn-Selective Synthesis of 4,4,4-Trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones
    Funabiki, Kazumasa
    Matsunaga, Kei
    Gonda, Hiroshi
    Yamamoto, Hitoshi
    Arima, Takao
    Kubota, Yasuhiro
    Matsui, Masaki
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01): : 285 - 288
  • [30] Metal-free protocol for the synthesis of novel 6-(het)aryl-5-aryl-5H-imidazo[4,5-b][1,2,5]oxadiazolo[3,4-e]pyrazines
    Kvashnin, Yuriy A.
    Rusinov, Gennady L.
    Charushin, Valery N.
    MENDELEEV COMMUNICATIONS, 2018, 28 (05) : 461 - 463
1234