Acidic ionic liquid [NMP]H2PO4 as dual solvent-catalyst for synthesis of β-alkoxyketones by the oxa-Michael addition reactions

被引:49
|
作者
Guo, Hui [1 ]
Li, Xia [1 ]
Wang, Jun-Liang [1 ]
Jin, Xiao-Han [1 ]
Lin, Xian-Fu [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
关键词
N-Methyl-2-pyrrolidonium; dihydrogen phosphate; oxa-Michael addition; Alcohols; Phenols; N-Substituted aminoethanols; EFFICIENT; ALKYLATION; GREEN; SYSTEM; HYDROALKOXYLATION; ESTERIFICATION; PALLADIUM(II); EQUIVALENT; COMPLEXES; HYDRATION;
D O I
10.1016/j.tet.2010.08.017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acidic ionic liquid N-methyl-2-pyrrolidonium dihydrogen phosphate [NMP]H2PO4 was prepared and used as efficient catalyst and reaction medium to synthesize beta-alkoxyketones by the oxa-Michael addition reactions for the first time. The effect of anions and cations, amount of ionic liquid on the reaction was investigated. Various alcohols and phenols proceeded smoothly and led to corresponding beta-alkoxyketones with high yields under mild reaction conditions, O-selectivity addition of amino-ethanols was also achieved in this paper. Compared with traditional imidazolium ionic liquids, [NMP] H2PO4 gave the better results. The ionic liquid was stable and could be reused at least five times with a slight loss of activity. (C) 2010 Published by Elsevier Ltd.
引用
收藏
页码:8300 / 8303
页数:4
相关论文
共 50 条
  • [1] Oxa-Michael Addition Reactions of 3-hydroxy-2-azetidinones: Synthesis of 1, 3, 4-Trisubstituted-2-Azetidinones
    Sharma, Priyanka
    Mann, Maninderjeet Kaur
    Bhargava, Gaurav
    LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (06) : 471 - 476
  • [2] Aggregation Behavior of Task-Specific Acidic Ionic Liquid N-Methyl-2-Pyrrolidinium Dihydrogen Phosphate [NMP][H2PO4] in Aqueous and Aqueous Salt Solutions
    Pal, Amalendu
    Saini, Mohit
    JOURNAL OF SURFACTANTS AND DETERGENTS, 2019, 22 (03) : 491 - 499
  • [3] Biocompatible ionic liquid [Betaine][H2PO4] as a reusable catalyst for the substitution of xanthen-9-ol under solvent-free conditions
    Zhu, Anlian
    Wang, Tong
    Feng, Wanlu
    Wang, Jianji
    Li, Lingjun
    RSC ADVANCES, 2020, 10 (52) : 31662 - 31669
  • [4] A new green approach for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one derivatives using task specific acidic ionic liquid[NMP]H2PO4
    Harjinder Singh
    Sudesh Kumari
    Jitender M.Khurana
    Chinese Chemical Letters, 2014, 25 (10) : 1336 - 1340
  • [5] A new green approach for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one derivatives using task specific acidic ionic liquid [NMP]H2PO4
    Singh, Harjinder
    Kumari, Sudesh
    Khurana, Jitender M.
    CHINESE CHEMICAL LETTERS, 2014, 25 (10) : 1336 - 1340
  • [6] 4-Imidazol-1-yl-butane-1-sulfonic acid ionic liquid: Synthesis, structural analysis, physical properties and catalytic application as dual solvent-catalyst
    Khaligh, Nader Ghaffari
    Mihankhah, Taraneh
    RafieJohan, Mohd
    Ching, Juan Joon
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (09) : 866 - 878
  • [7] Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 using ionic liquids as a dual solvent-catalyst at atmospheric pressure
    Lu, Wenjing
    Ma, Jun
    Hu, Jiayin
    Song, Jinliang
    Zhang, Zhaofu
    Yang, Guanying
    Han, Buxing
    GREEN CHEMISTRY, 2014, 16 (01) : 221 - 225
  • [8] Synthesis of 1,8-dioxo-octahydroxanthenes and bis(indolyl)methanes catalyzed by [Et3NH][H2PO4] as a cheap and mild acidic ionic liquid
    Kalantari, Maryam
    ARABIAN JOURNAL OF CHEMISTRY, 2012, 5 (03) : 319 - 323
  • [9] Synthesis of 1,4-Dihydroquinolines and 4H-Chromenes via Organocatalytic Domino Aza/Oxa-Michael/1,6-Addition Reactions of para-Quinone Methides and Ynals
    Wang, Junwei
    Rong, Quanjin
    Zhao, Lei
    Pan, Xiang
    Zhao, Lin
    Zhao, Kun
    Hu, Lihong
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (17): : 11240 - 11249
  • [10] Synthesis of a series of novel dihydro-[1,2,4]triazolo [1,5-a]pyrimidine scaffolds: Dual solvent-catalyst activity of a low viscous and acid-functionalized ionic liquid
    Zaharani, Lia
    Khaligh, Nader Ghaffari
    Mihankhah, Taraneh
    Shahnavaz, Zohreh
    Johan, Mohd Rafie
    SYNTHETIC COMMUNICATIONS, 2020, 50 (11) : 1633 - 1640