Three-component reaction of 2-alkynylbenzaldehyde, amine, and nucleophile using Lewis acid-surfactant combined catalyst in water

被引:74
|
作者
Ye, Yang [1 ]
Ding, Qiuping [1 ,3 ]
Wu, He [1 ,2 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[3] Jiangxi Normal Univ, Analyt Ctr Phys & Chem, Nanchang 330027, Peoples R China
基金
中国国家自然科学基金;
关键词
Lewis acid-surfactant combined catalyst; water; ultrasonic; 1,2-dihydroisoquinoline;
D O I
10.1016/j.tet.2007.11.055
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lewis acid-surfactant combined catalyst (LASC) catalyzed three-component reactions of 2-alkynylbenzaldehyde, amines, and nucleophiles (alkyne, nitromethane, or diethyl phosphate) in water under ultrasonic conditions afforded the corresponding 1,2-dihydroisoquinoline derivatives in good yields. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1378 / 1382
页数:5
相关论文
共 50 条
  • [31] Catalyst-free three-component reaction between 2-aminopyridines (or 2-aminothiazoles), aldehydes, and isocyanides in water
    Adib, Mehdi
    Mahdavi, Mohammad
    Noghani, Mahsa Alizadeh
    Mirzaei, Peiman
    TETRAHEDRON LETTERS, 2007, 48 (41) : 7263 - 7265
  • [32] A novel synthesis of 2-aminopyrroles using a three-component reaction
    Nair, V
    Vinod, AU
    Rajesh, C
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12): : 4427 - 4429
  • [33] Lewis Acid Catalyzed Three-Component [3+2] Cycloaddition Reaction Using Pentafulvene as 2π Component: An Easy Way to Construct Pentaleno(1,2-b)indoles
    Santhini, P. V.
    Chand, S. Sarath
    John, Jubi
    Varma, R. Luxmi
    Jaroschik, Florian
    Radhakrishnan, K. V.
    SYNLETT, 2017, 28 (08) : 951 - 956
  • [34] Dehydrative glycosylation in water using a bronsted acid-surfactant-combined catalyst
    Aoyama, N
    Kobayashi, S
    CHEMISTRY LETTERS, 2006, 35 (02) : 238 - 239
  • [35] Acid-ionic polymer as recyclable catalyst for one-pot three-component Mannich reaction
    Senapak, W.
    Saeeng, R.
    Sirion, U.
    RSC ADVANCES, 2017, 7 (48): : 30380 - 30384
  • [36] A Highly Diastereoselective Synthesis of α-Hydroxy-β-amino Acid Derivatives via a Lewis Acid Catalyzed Three-Component Condensation Reaction
    Gassa, Federico
    Contini, Alessandro
    Fontana, Gabriele
    Pellegrino, Sara
    Gelmi, Maria Luisa
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7099 - 7106
  • [37] Utilization of Solid Acid SO42-/TiO2 as Catalyst to the Three-Component Mannich Reaction at Ambient Temperature
    Yao, Yuanyong
    Zhang, Meng
    Chen, Shixue
    Xing, Mingming
    Shu, Hua
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (04) : 2520 - 2528
  • [38] Facile synthesis of ninhydrin and isatin based hydrazones in water using PEG-OSO3H as a highly efficient and homogeneous polymeric acid-surfactant combined catalyst
    Debnath, Kamalesh
    Pathak, Sudipta
    Pramanik, Animesh
    TETRAHEDRON LETTERS, 2013, 54 (31) : 4110 - 4115
  • [39] Synthesis of (Z)-1-benzylidene-3-(1H-indol-1-yl)-1H-indene-2,2(3H)-dicarbonitriles via three-component reaction of 2-alkynylbenzaldehyde, malononitrile, and indole
    Qiu, Guanyinsheng
    Ding, Qiuping
    Peng, Yiyuan
    Wu, Jie
    TETRAHEDRON LETTERS, 2010, 51 (33) : 4391 - 4394
  • [40] Microwave-Assisted Decarboxylative Three-Component Coupling of a 2-Oxoacetic Acid, an Amine, and an Alkyne
    Feng, Huangdi
    Ermolat'ev, Denis S.
    Song, Gonghua
    Van der Eycken, Erik V.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18): : 7608 - 7613