An Efficient Synthesis of 2-Aminofuran-3-carbonitriles via Cascade Stetter-γ-Ketonitrile Cyclization Reaction Catalyzed by N-Heterocyclic Carbene

被引：24
|
作者：
Liu, Peng [1 ]
Lei, Min [1 ]
Ma, Lei [1 ]
Hu, Lihong [1 ,2 ]
机构：
[1] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
[2] Shanghai Inst Mat Med, Shanghai Res Ctr Modernizat Tradit Chinese Med, Shanghai 201203, Peoples R China
来源：
SYNLETT | 2011年 / 08期
基金：
中国国家自然科学基金;
关键词：
N-heterocyclic carbenes (NHCs); umpolung; cascade reaction; Stetter reaction; 2-aminofuran; CONJUGATE UMPOLUNG; BENZOIN REACTIONS; ALDEHYDES; ACYLOIN; TANDEM;
D O I：
10.1055/s-0030-1259945
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of 4,5-disubstituted 2-aminofuran-3-carbonitriles via a cascade Stetter-gamma-ketonitrile cyclization reaction of aromatic aldehydes with acylidenemalononitriles, catalyzed by N-heterocyclic carbenes, has been developed. This procedure provides the corresponding products in moderate to high yields under mild conditions.
引用
收藏
页码：1133 / 1136
页数：4
相关论文
共 50 条
  • [1] Construction of Bisbenzopyrone via N-Heterocyclic Carbene Catalyzed Intramolecular Hydroacylation-Stetter Reaction Cascade
    Zhao, Ming
    Liu, Jia-Lin
    Liu, Hang-Fan
    Chen, Jie
    Zhou, Ling
    ORGANIC LETTERS, 2018, 20 (09) : 2676 - 2679
  • [2] Efficient Synthesis of Benzofuranones: N-Heterocyclic Carbene (NHC)/Base-Catalyzed Hydroacylation-Stetter-Rearrangement Cascade
    Padmanaban, Mohan
    Biju, Akkattu T.
    Glorius, Frank
    ORGANIC LETTERS, 2011, 13 (20) : 5624 - 5627
  • [3] Efficient N-Heterocyclic Carbene-Catalyzed Cascade Synthesis of Functionalized Naphthopyranone
    Li, Sha
    Xu, Jiayu
    Luo, Xian
    Yang, Wenhan
    Yao, Changsheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (02) : 470 - 477
  • [4] Computational Study on N-Heterocyclic Carbene (NHC)-Catalyzed Intramolecular Hydroacylation-Stetter Reaction Cascade
    Liu, Qiuli
    Wang, Yang
    Wang, Yanyan
    Li, Xue
    Qu, Ling-Bo
    Lan, Yu
    Wei, Donghui
    MOLECULAR CATALYSIS, 2020, 484
  • [5] Enantioselective Synthesis of Bicyclic δ-Lactones via N-Heterocyclic Carbene-Catalyzed Cascade Reaction
    Liang, Zhi-Qin
    Wang, Dong-Ling
    Zhang, Han-Ming
    Ye, Song
    ORGANIC LETTERS, 2015, 17 (20) : 5140 - 5143
  • [6] Diastereoselective Synthesis of 4-Hydroxytetralones via a Cascade Stetter-Aldol Reaction Catalyzed by N-Heterocyclic Carbenes
    Sun, Fang-Gang
    Huang, Xue-Liang
    Ye, Song
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) : 273 - 276
  • [7] α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals
    Wang, Xu
    Wu, Zijun
    Wang, Jian
    ORGANIC LETTERS, 2016, 18 (03) : 576 - 579
  • [8] Role of base assisted proton transfer in N-heterocyclic carbene-catalyzed intermolecular Stetter reaction
    Ajitha, Manjaly J.
    Suresh, Cherumuttathu H.
    TETRAHEDRON LETTERS, 2013, 54 (52) : 7144 - 7146
  • [9] N-Heterocyclic carbene-catalyzed synthesis of acetyltributylcitrate via a transesterification reaction
    He, Lin
    Guo, Hao
    Ma, Xiao-Wei
    Zhang, Jie
    Gu, Cheng-Zhi
    Wang, Wei
    Dai, Bin
    CHINESE CHEMICAL LETTERS, 2014, 25 (02) : 215 - 217
  • [10] N-Heterocyclic Carbene Catalyzed Asymmetric Intermolecular Stetter Reaction: Origin of Enantioselectivity and Role of Counterions
    Kuniyil, Rositha
    Sunoj, Raghavan B.
    ORGANIC LETTERS, 2013, 15 (19) : 5040 - 5043
12345