N-Heterocyclic Carbene Catalyzed Aroylation of 3,5-Dichloro-2 (1H)-pyrazinones

被引：18
|
作者：
Mehta, Vaibhav P. [1 ]
Sharma, Ajendra Kumar [1 ]
Modha, Sachin G. [1 ]
Sharma, Sweta [1 ,2 ]
Meganathan, Thirumal [2 ]
Parmar, Virinder Singh [2 ]
Van der Eycken, Erik [1 ]
机构：
[1] Katholieke Univ Leuven, Dept Chem, LOMAC, B-3001 Louvain, Belgium
[2] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 100007, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 08期
关键词：
AROMATIC-ALDEHYDES; 2(1H)-PYRAZINONES; THIOETHERS; MECHANISM; ENALS;
D O I：
10.1021/jo200155n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The N-heterocyclic carbene catalyzed chemoselective C3-aroylation of 3,5-dichloro-2(1H)-pyrazinones with various aldehydes is reported. We herein describe results of this remarkable mild and efficient procedure.
引用
收藏
页码：2920 / 2925
页数：6
相关论文
共 50 条
  • [1] Alkylation of 3,5-dichloro-2(1H)-pyrazinones using malonate esters
    Mishra, Nigam M.
    Peshkov, Vsevolod A.
    Pereshivko, Olga P.
    Modha, Sachin G.
    Van der Eycken, Erik V.
    TETRAHEDRON LETTERS, 2012, 53 (35) : 4676 - 4678
  • [2] N-heterocyclic carbene-catalyzed nucleophilic aroylation of fluorobenzenes
    Suzuki, Yumiko
    Ota, Shinya
    Fukuta, Yoshinori
    Ueda, Yuki
    Sato, Masayuki
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06): : 2420 - 2423
  • [3] A straightforward microwave method for rapid synthesis of N-1, C-6 functionalized 3,5-dichloro-2(1H)-pyrazinones
    Gising, Johan
    Ortqvist, Pernilla
    Sandstrom, Anja
    Larhed, Mats
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (13) : 2809 - 2815
  • [4] Efficient and Selective Palladium-Catalysed C-3 Urea Couplings to 3,5-Dichloro-2(1H)-pyrazinones
    Belfrage, Anna Karin
    Gising, Johan
    Svensson, Fredrik
    Akerblom, Eva
    Skold, Christian
    Sandstrom, Anja
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (05) : 978 - 986
  • [5] One-pot synthesis of unsymmetrical benzils and N-heteroarenes through nucleophilic aroylation catalyzed by N-heterocyclic carbene
    Suzuki, Yumiko
    Murofushi, Mai
    Manabe, Kei
    TETRAHEDRON, 2013, 69 (02) : 470 - 473
  • [6] Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by N-heterocyclic carbene at atmospheric pressure
    Xiao, Yunqing
    Kong, Xianqiang
    Xu, Zhicheng
    Cao, Changsheng
    Pang, Guangsheng
    Shi, Yanhui
    RSC ADVANCES, 2015, 5 (07) : 5032 - 5037
  • [7] N-Heterocyclic Carbene Catalyzed Deuteration of Aldehydes in D 2 O
    Sawama, Yoshinari
    Miki, Yuya
    Sajiki, Hironao
    SYNLETT, 2020, 31 (07) : 699 - 702
  • [8] N-Heterocyclic Carbene Catalyzed Stereoselective Glycosylation of 2-Nitrogalactals
    Liu, Jia-Lin
    Zhang, Yu -Tong
    Liu, Hang-Fan
    Zhou, Ling
    Chen, Jie
    ORGANIC LETTERS, 2017, 19 (19) : 5272 - 5275
  • [9] 3,5-dihalo-2(1H)-pyrazinones:: Versatile scaffolds in organic synthesis
    Pawar, Vijaykumar G.
    De Borggraeve, Wim M.
    SYNTHESIS-STUTTGART, 2006, (17): : 2799 - 2814
  • [10] N-Heterocyclic carbene-catalyzed remote C(sp3)-H acylation of amides
    Xu, Huiwei
    Mo, Jia-Nan
    Liu, Wen -Deng
    Zhao, Jiannan
    TETRAHEDRON LETTERS, 2023, 121
12345