Simple and Efficient Preparation of 2,5-Disubstituted Oxazoles via a Metal-Free-Catalyzed Cascade Cyclization

被引：147
|
作者：
Wan, Changfeng
Gao, Linfeng
Wang, Qiang
Zhang, Jintang
Wang, Zhiyong [1 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Soft Matter Chem, Hefei 230026, Peoples R China
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 17期
关键词：
SP(3) C-H; DIRECT ARYLATION; COPPER; INHIBITORS; OXIDATION;
D O I：
10.1021/ol101596s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical and simple synthesis of 2,5-disubstituted oxazoles was developed via an iodine-catalyzed tandem oxidative cyclization. A wide range of common commercial aromatic aldehydes can be used as reaction substrates, which displayed excellent functional group compatibility in this reaction.
引用
收藏
页码：3902 / 3905
页数：4
相关论文
共 50 条
  • [41] A review on synthetic routes for obtaining of 2,5-disubstituted 1,3,4-oxadiazoles via cyclodehydration and oxidative cyclization reactions
    Lelyukh, Maryan
    Demchuk, Inna
    Harkov, Stefan
    Chaban, Taras
    Drapak, Iryna
    Chaban, Ihor
    Shelepeten, Lesya
    Matiychuk, Vasyl
    BIOINTERFACE RESEARCH IN APPLIED CHEMISTRY, 2020, 10 (04): : 5960 - 5971
  • [42] Synthesis of 2,5-Disubstituted Furans via Palladium-Catalyzed Annulation of Alkyl 3-Oxo-6-heptynoates
    Cacchi, S.
    Fabrizi, G.
    Moro, L.
    Journal of Organic Chemistry, 62 (16):
  • [43] Synthesis of 2,5-disubstituted furans via palladium-catalyzed annulation of alkyl 3-oxo-6-heptynoates
    Cacchi, S
    Fabrizi, G
    Moro, L
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16): : 5327 - 5332
  • [44] Iodoarene-mediated one-pot preparation of 2,5-disubstituted and 2,4,5-trisubstituted oxazoles from alkyl aryl ketones with oxone in nitriles
    Ishiwata, Yoshihide
    Togo, Hideo
    TETRAHEDRON, 2009, 65 (51) : 10720 - 10724
  • [45] Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions
    Zhang, Guofu
    Yu, Yidong
    Zhao, Yiyong
    Xie, Xiaoqiang
    Ding, Chengrong
    SYNLETT, 2017, 28 (11) : 1373 - 1377
  • [46] One-pot preparation of 2,5-disubstituted and 2,4,5-trisubstituted oxazoles from aromatic ketones with molecular iodine, oxone, and trifluoromethanesulfonic acid in nitriles
    Imai, Sho
    Kikui, Hiroki
    Moriyama, Katsuhiko
    Togo, Hideo
    TETRAHEDRON, 2015, 71 (33) : 5267 - 5274
  • [47] Copper(I)-Catalyzed A3-Coupling Based Reaction of Alkynes, Aldehydes, and Amines: An Efficient Approach to 2,5-Polysubstituted Dihydrofurans and 2,5-Disubstituted Furans
    Fan, Wu
    Ma, Shengming
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (16) : 3531 - 3539
  • [48] FACILE SYNTHESIS OF 2,5-DISUBSTITUTED FURANS VIA PALLADIUM COMPLEX AND PERFLUORINATED RESINSULFONIC ACID-CATALYZED ISOMERIZATION DEHYDRATION OF ALKYNEDIOLS
    JI, JG
    LU, XY
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (09) : 764 - 765
  • [49] One-pot cyclization/decarboxylation of α-keto acids and acylhydrazines for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under transition-metal-free conditions
    Gao, Peng
    Wang, Juan
    Bai, Zijing
    Cheng, Hualei
    Xiao, Jian
    Lai, Mengnan
    Yang, Desuo
    Fan, Mingjin
    TETRAHEDRON LETTERS, 2016, 57 (41) : 4616 - 4619
  • [50] An efficient synthesis of 2,5-diimino-furans via Pd-catalyzed cyclization of bromoacrylamides and isocyanides
    Jiang, Huanfeng
    Yin, Meizhou
    Li, Yibiao
    Liu, Bifu
    Zhao, Jinwu
    Wu, Wanqing
    CHEMICAL COMMUNICATIONS, 2014, 50 (16) : 2037 - 2039
12345