Zinc chloride catalyzed three-component Ugi reaction: synthesis of N-cyclohexyl-2-(2-hydroxyphenylamino)acetamide derivatives

被引:35
|
作者
Shaabani, Ahmad [1 ]
Keshipour, Sajjad [1 ]
Shaabani, Shabnam [1 ]
Mahyari, Mojtaba [1 ]
机构
[1] Shahid Beheshti Univ, Dept Chem, GC, Tehran, Iran
关键词
Three-component Ugi reaction; Zinc chloride; Acetamide; Isocyanide; AMINO-ACID AMIDES; ANTICONVULSANT ACTIVITY; CONDENSATION REACTION; MULTICOMPONENT REACTIONS; ISOCYANIDES;
D O I
10.1016/j.tetlet.2012.01.079
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ability of zinc chloride as a catalyst to promote the three-component Ugi reaction of 2-aminophenols, aliphatic or aromatic aldehydes, and cyclohexyl isocyanide in methanol at room temperature is described. The N-cyclohexyl-2-(2-hydroxyphenylamino) amide products are obtained in high yields. When N,N-dimethylformamide dimethyl acetal and triethyl orthoformate, as two new components of the three-component Ugi reaction are used instead of the aldehyde the reaction gives N-cyclohexyl-2-(dimethylamino)-2-(2-hydroxyphenylamino)acetamide and N-cyclohexyl-2-(2-hydroxyphenylamino)-2-ethoxyacetamide derivatives, respectively. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1641 / 1644
页数:4
相关论文
共 50 条
  • [1] A novel gabapentin based intermolecular Ugi four-center, three-component reaction for preparing N-cyclohexyl-2-(3-oxo-2-azaspiro[4,5]decan-2-yl)-2-aryl acetamide derivatives
    Darehkordi, Ali
    Zand-Vakili, Fatemeh
    Rafsanjani, Alireza Talebizadeh
    TETRAHEDRON LETTERS, 2016, 57 (04) : 498 - 501
  • [2] Synthesis and Antifungal Activity of New N-Aryl-2-(2-hydroxyphenylamino)ethylenediamine Derivatives
    Han Gao
    Yichao Wan
    Yuhuan Tan
    Xi Luo
    Lin Li
    Russian Journal of General Chemistry, 2021, 91 : 122 - 127
  • [3] Synthesis and Antifungal Activity of New N-Aryl-2-(2-hydroxyphenylamino)ethylenediamine Derivatives
    Gao, Han
    Wan, Yichao
    Tan, Yuhuan
    Luo, Xi
    Li, Lin
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2021, 91 (01) : 122 - 127
  • [4] A novel three-component reaction for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amines
    Heravi, Majid M.
    Baghernejad, Bita
    Oskooie, Hossein A.
    TETRAHEDRON LETTERS, 2009, 50 (07) : 767 - 769
  • [5] An efficient synthesis of 2,5-diketopiperazine derivatives by the Ugi four-center three-component reaction
    Sangwon Cho
    Gyochang Keum
    Soon Bang Kang
    So-Yeop Han
    Youseung Kim
    Molecular Diversity, 2003, 6 : 283 - 286
  • [6] An efficient synthesis of 2,5-diketopiperazine derivatives by the Ugi four-center three-component reaction
    Cho, Sangwon
    Keum, Gyochang
    Kang, Soon Bang
    Han, So-Yeop
    Kim, Youseung
    MOLECULAR DIVERSITY, 2003, 6 (3-4) : 283 - 286
  • [7] Organocatalytic Synthesis of α,α-Diaryl Substituted α-Amino Acid Derivatives by an Interrupted Three-Component Ugi Reaction
    Glavac, Danijel
    Jeric, Ivanka
    Gredicak, Matija
    CROATICA CHEMICA ACTA, 2019, 92 (02) : 203 - 209
  • [8] Synthesis of Propargylamine and Indolazine Derivatives via Three-Component Reaction Catalyzed by CuOx/CeO2 Materials
    Wang, Haorui
    Shi, Dapeng
    Meng, Yuhang
    Hai, Mengya
    Shu, Yan
    Liu, Binyuan
    Duan, Zhongyu
    CHEMISTRYSELECT, 2023, 8 (34):
  • [9] Reaction of N-cyclohexyl-2-(2-hydroxynaphthalen-1-yl)pyrrolidine-1-carboxamide with resorcinol and its derivatives and synthesis of polyphenols
    Smolobochkin A.V.
    Gazizov A.S.
    Burilov A.R.
    Pudovik M.A.
    Russian Chemical Bulletin, 2016, 65 (5) : 1377 - 1379
  • [10] Fe-Catalyzed Three-Component Reaction for the Synthesis of 2,3′-Biquinolines
    Xiao, Fuhong
    Yang, Gang
    Yao, Lin
    Mao, Guojiang
    Deng, Guo-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (20) : 3501 - 3505