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
  • [41] N-Heterocyclic carbene catalyzed tail-to-tail oligomerization of N,N-dimethylacrylamide (DMAA) and the search for the Stetter reaction of DMAA with benzaldehyde
    Rajachan, Oue-artom
    Paul, Mathias
    Yatham, Veera Reddy
    Neudoerfl, Joerg-M.
    Kanokmedhakul, Kwanjai
    Kanokmedhakul, Somdej
    Berkessel, Albrecht
    TETRAHEDRON LETTERS, 2015, 56 (47) : 6537 - 6540
  • [42] N-Heterocyclic Carbene (NHC)-Catalyzed Intramolecular Stetter Reaction to Access Dibenzo-fused Seven-membered Heterocycles
    Yadav, Sanjay
    Suresh, Surisetti
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (06) : 1406 - 1409
  • [43] Construction of N-Polyheterocycles by N-Heterocyclic Carbene Catalysis via a Regioselective Intramolecular Radical Addition/Cyclization Cascade
    Zhang, Qijing
    Lei, Hao
    Zhou, Cong-Ying
    Wang, Chengming
    ORGANIC LETTERS, 2022, 24 (25) : 4615 - 4619
  • [44] Synthesis of Pyrroloindolines via N-Heterocyclic Carbene Catalyzed Dearomative Amidoacylation of Indole Derivatives
    Shu, Hanyu
    Mo, Jia-Nan
    Liu, Wen-Deng
    Zhao, Jiannan
    ORGANIC LETTERS, 2023, 25 (48) : 8677 - 8682
  • [45] N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Dihydropyranothiazoles via Azolium Enolate Intermediates
    Li, Sun
    Chen, Xiang-Yu
    Sheng, He
    von Essen, Carolina
    Rissanen, Kari
    Enders, Dieter
    SYNTHESIS-STUTTGART, 2018, 50 (05): : 1047 - 1052
  • [46] Aerobic Oxidative N-Heterocyclic Carbene-Catalyzed Formal [3+3] Cyclization for the Synthesis of Tetrasubstituted Benzene Derivatives
    Bacaicoa, Sara
    Goossens, Ellymay
    Sunden, Henrik
    ORGANIC LETTERS, 2022, 24 (49) : 9146 - 9150
  • [47] N-Heterocyclic Carbene Catalyzed Synthesis of δ-Sultones via α,β-Unsaturated Sulfonyl Azolium Intermediates
    Ungureanu, Andrei
    Levens, Alison
    Candish, Lisa
    Lupton, David W.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (40) : 11780 - 11784
  • [48] N-Heterocyclic Carbene Catalyzed [2+2] Cycloaddition of Aryl Isothiocyanates and Nitroolefins: An Efficient Synthesis of β-Thiolactams
    Awasthi, Chhama
    Yadav, Lal Dhar S.
    SYNLETT, 2010, (12) : 1783 - 1788
  • [49] N-Heterocyclic Carbene Catalyzed Stereoselective Synthesis of 2-Nitro-thiogalactosides
    Hu, Yu-Long
    Gou, Bo-Bo
    Wang, Jiao
    Zhao, Ming
    Liu, Jia-Lin
    Chen, Jie
    Zhou, Ling
    SYNTHESIS-STUTTGART, 2019, 51 (18): : 3451 - 3461
  • [50] Enantioselective synthesis of 4-aryl-3,4-dihydrocoumarins via N-heterocyclic carbene catalyzed β-arylation/cyclization of α-bromoenals
    Liang, Yu-Jing
    Gao, Yuan-Yuan
    Han, Hua-Bo
    Li, Lu
    Liu, Lantao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (25) : 5101 - 5104
12345