Indium(III) iodide-mediated Strecker reaction in water:: an efficient and environmentally friendly approach for the synthesis of α-aminonitrile via a three-component condensation

被引:85
|
作者
Shen, Zhi-Liang [1 ,2 ]
Ji, Shun Jun [1 ]
Loh, Teck-Peng [2 ]
机构
[1] Suzhou Soochow Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
基金
中国国家自然科学基金;
关键词
Strecker reaction; alpha-aminonitrile; indium(III) iodide; water; three-component reaction;
D O I
10.1016/j.tet.2008.06.047
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild, efficient and environmentally friendly method has been developed for the synthesis of alpha-aminonitriles via a three-component condensation of aldehyde, amine and TMSCN in the presence of a catalytic amount of indium(III) iodide in water. The reactions proceeded smoothly at room temperature in water to generate the corresponding products in moderate to excellent yields. (C) 2008 Published by Elsevier Ltd.
引用
收藏
页码:8159 / 8163
页数:5
相关论文
共 50 条
  • [11] A novel one-pot three-component synthesis of benzofuran derivatives via Strecker reaction: Study of antioxidant activity
    Ezzatzadeh, Elham
    Hossaini, Zinatossadat
    NATURAL PRODUCT RESEARCH, 2020, 34 (07) : 923 - 929
  • [12] One-pot, three-component condensation reaction in water: An efficient and improved procedure for the synthesis of pyran annulated heterocyclic systems
    Shaabani, Ahmad
    Samadi, Sima
    Rahmati, Abbas
    SYNTHETIC COMMUNICATIONS, 2007, 37 (1-3) : 491 - 499
  • [13] Facile access to -acyloxyamides via epoxide rearrangement/three-component domino reaction catalyzed by indium(III) chloride
    Lingaswamy, Kadari
    Krishna, Palakodety Radha
    Prapurna, Y. Lakshmi
    SYNTHETIC COMMUNICATIONS, 2016, 46 (15) : 1275 - 1282
  • [14] Synthesis and Antitumor Activity of Novel Coumarin Derivatives via a Three-component Reaction in Water
    Chen, Zhiwei
    Bi, Jianhao
    Su, Weike
    CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (04) : 507 - 514
  • [15] Lewis base-catalyzed three-component Strecker reaction on water. An efficient manifold for the direct α-cyanoamination of ketones and aldehydes
    Cruz-Acosta, Fabio
    Santos-Exposito, Alicia
    de Armas, Pedro
    Garcia-Tellado, Fernando
    CHEMICAL COMMUNICATIONS, 2009, (44) : 6839 - 6841
  • [16] An efficient and green synthesis of ferrocenyl-quinoline conjugates via a TsOH-catalyzed three-component reaction in water
    Mou, Rui-Qi
    Zhao, Mei
    Lv, Xue-Xin
    Zhang, Sheng-Yan
    Guo, Dian-Shun
    RSC ADVANCES, 2018, 8 (17): : 9555 - 9563
  • [17] DABCO-catalyzed efficient synthesis of naphthopyran derivatives via one-pot three-component condensation reaction at room temperature
    Balalaie, Saeed
    Ramezanpour, Sorour
    Bararjanian, Morteza
    Gross, Juergen H.
    SYNTHETIC COMMUNICATIONS, 2008, 38 (07) : 1078 - 1089
  • [18] A simple and effective approach to the synthesis of rhodanine derivatives via three-component reactions in water
    Alizadeh, Abdolati
    Rostamnia, Sadegh
    Zohreh, Nasrin
    Hosseinpour, Reza
    TETRAHEDRON LETTERS, 2009, 50 (14) : 1533 - 1535
  • [19] An efficient and convenient approach to the synthesis of benzopyrans by a three-component coupling of one-pot reaction
    Jin, TS
    Xiao, JC
    Wang, SJ
    Li, TS
    Song, XR
    SYNLETT, 2003, (13) : 2001 - 2004
  • [20] A crystalline Sm(III)-containing antimonotungstate with efficient catalytic activity in three-component reaction for isoindolinones synthesis
    Liu, Hao-Qi
    Cao, Jia-Wei
    Tang, Wei
    Lin, Zhou-Fu
    Li, Ke
    Xu, Wei-Jian
    Zhang, Zhi-Bin
    Liu, Yu-Feng
    Yang, Guo-Ping
    RARE METALS, 2025,