Lewis Acid-Promoted Three-Component Cyclization for the Construction of Functionalized Oxazoles

被引：10
|
作者：
Li, Anquan [1 ,2 ]
Zhao, Jun [1 ,2 ]
Zhang, Chen [1 ,2 ]
Jiang, Qiuxia [1 ,2 ]
Zhu, Baofu [1 ,2 ]
Cao, Hua [1 ,2 ]
机构：
[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Zhongshan 528458, Peoples R China
[2] Guangdong Pharmaceut Univ, Guangdong Cosmet Engn & Technol Res Ctr, Zhongshan 528458, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期
关键词：
VINYL SULFONES; PROPARGYLIC AMIDES; BOND FORMATION; C-S; ACCESS; SULFONYLATION; INHIBITORS; ASCIDIANS; DISCOVERY; AGENTS;
D O I：
10.1021/acs.joc.2c01432
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient synthetic strategy from amides, ynals, and sodium sulfinates via a Lewis acid-promoted threecomponent reaction has been reported. Thus, a broad range of various aryl (not alkyl)-substituted oxazoles could be synthesized via the formation of C-N, C-O, and C-S bonds in a one-pot process. In addition, this reaction possesses other unique advantages, such as transition metal-free catalysis, high step economy, good functional group tolerance, and good regioselectivity.
引用
收藏
页码：27 / 38
页数：12
相关论文
共 50 条
  • [21] Lewis acid-promoted reactions of zirconacyclopentadienes with isocyanates. A one-pot three-component synthesis of multiply-substituted iminocyclopentadienes from one isocyanate and two alkynes
    Lu, J
    Mao, GL
    Zhang, WX
    Xi, ZF
    CHEMICAL COMMUNICATIONS, 2005, (38) : 4848 - 4850
  • [22] Bronsted acid-promoted three-component reaction of 2-methoxythiophene, sulfinates and water: Synthesis of γ-mercapto-β-sulfonyl esters
    Chen, Xianlie
    Luo, Yixin
    Zeng, Qingle
    TETRAHEDRON LETTERS, 2022, 100
  • [23] A NaHCO3 Promoted Three-component Cyclization: Easy Access to Benzodisulfide Heterocycles
    Zhou, Yong-Jun
    Yang, Kai
    Fang, Yong-Gan
    Luo, Shi-He
    Chen, Qi
    Yu, Shi-Wei
    Wang, Zhao-Yang
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (06)
  • [24] Lewis acid-promoted reactions of γ-lactols with silyl enol ethers -: Stereoselective formation of functionalized tetrahydrofuran derivatives
    Schmitt, A
    Reissig, HU
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (06) : 1169 - 1174
  • [25] The Lewis Acid-promoted Novel Cyclization Reactions Towards N-adn O-Containing Heterocycles
    Shoko Yamazaki
    复旦学报(自然科学版), 2007, (05) : 588 - 588
  • [26] An unexpected allyl-transfer reaction under conditions of Lewis acid-promoted cyclization of homoallylic alcohols with aldehydes
    Samoshin, VV
    Smoliakova, IP
    Hank, MM
    Gross, PH
    MENDELEEV COMMUNICATIONS, 1999, (06) : 219 - 221
  • [27] Tetrahydroquinolines by Lewis Acid-promoted Friedel-Crafts Cyclizations
    Bunce, Richard A.
    Cain, Nicholas R.
    Cooper, John G.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2013, 45 (01) : 28 - 43
  • [28] Catalytic Three-Component Domino Reaction for the Preparation of Trisubstituted Oxazoles
    v Wachenfeldt, Henrik
    Roese, Philipp
    Paulsen, Filip
    Loganathan, Nagarajan
    Strand, Daniel
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (24) : 7982 - 7988
  • [29] Lewis acid-promoted site-selective cyanation of phenols
    Zhang, Wu
    Yang, Wen
    Zhao, Wanxiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (24) : 4604 - 4609
  • [30] Lewis acid-promoted α-hydroxy β-dicarbonyl to α-ketol ester rearrangement
    Hong, Xuechuan
    Mejia-Oneto, Jose M.
    Padwa, Albert
    TETRAHEDRON LETTERS, 2006, 47 (47) : 8387 - 8390
12345