One-Pot Three-Component Synthesis of Hantzsch 1,4-Dihydropyridines Promoted by Dimethyl Phosphate Ionic Liquids

被引：7
|
作者：
Priede, Elina [1 ]
Zicmanis, Andris [1 ]
机构：
[1] Univ Latvia, Fac Chem, LV-1586 Riga, Latvia
来源：
HELVETICA CHIMICA ACTA | 2015年 / 98卷 / 08期
关键词：
Hantzsch; 1; 4-dihydropyridines; Dimethyl phosphate; Ionic liquids; Three-component reactions; SOLVENT-FREE SYNTHESIS; EFFICIENT SYNTHESIS; POLYHYDROQUINOLINE DERIVATIVES; PYRIDINE CONDENSATION; AROMATIC-ALDEHYDES; HYDROGEN SULFATE; CATALYST; DIHYDROPYRIDINES; BENZALDEHYDES; REDUCTION;
D O I：
10.1002/hlca.201500009
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A one-pot three-component reaction of ethyl acetoacetate, AcONH4, and different aldehydes has been successfully performed in the presence of ionic liquids (ILs) possessing a (MeO)(2)PO2- counterion. The impact of electronic and steric effects of the substituents of aromatic aldehydes, as well as the influence of different anions of ILs on the product yield, have been investigated. The application of dimethyl phosphate ILs in the synthesis of Hantzsch 1,4-dihydropyridines presents a simple method for obtaining structurally diverse products in moderate to high yields without using any additional catalyst.
引用
收藏
页码：1095 / 1103
页数：9
相关论文
共 50 条
  • [21] PEG1000-Based Dicationic Acidic Ionic Liquid Catalyzed One-pot Synthesis of 1,4-Dihydropyridines via the Hantzsch Reaction
    Ren, Yi-Ming
    Shao, Juan-Juan
    Wu, Zhi-Chuan
    Xu, Mao-Dong
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2014, 46 (06) : 545 - 550
  • [22] ONE-POT, THREE-COMPONENT SYNTHESIS OF α-AMINOPHOSPHONATES CATALYZED BY ACYCLIC ACIDIC IONIC LIQUIDS
    Fang, Dong
    Jiao, Changmei
    Ji, Baohua
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (12) : 2520 - 2526
  • [23] Alginic acid: a highly efficient renewable and heterogeneous biopolymeric catalyst for one-pot synthesis of the Hantzsch 1,4-dihydropyridines
    Dekamin, Mohammad G.
    Ilkhanizadeh, Siamand
    Latifidoost, Zahra
    Daemi, Hamed
    Karimi, Zahra
    Barikani, Mehdi
    [J]. RSC ADVANCES, 2014, 4 (100) : 56658 - 56664
  • [24] Molecular iodine-catalyzed one-pot synthesis of some new Hantzsch 1,4-dihydropyridines at ambient temperature
    Akbari, J. D.
    Tala, S. D.
    Dhaduk, M. F.
    Joshi, H. S.
    [J]. ARKIVOC, 2008, : 126 - +
  • [25] Silica gel/NaHSo4 catalyzed one-pot synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature
    Chari, MA
    Syamasundar, K
    [J]. CATALYSIS COMMUNICATIONS, 2005, 6 (09) : 624 - 626
  • [26] An Efficient, Three-component One-pot Preparation of 1,4-Dihydropyridines Containing Novel Substituted Pyrazole under Sulfamic Acid Catalysis
    Li Jianping
    Qiu Jikuan
    Li Huijuan
    Zhang Guisheng
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (03) : 511 - 514
  • [27] Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst
    Maleki A.
    Kamalzare M.
    Aghaei M.
    [J]. Journal of Nanostructure in Chemistry, 2015, 5 (1) : 95 - 105
  • [28] One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility
    Evdokimov, NM
    Magedov, IV
    Kireev, AS
    Kornienko, A
    [J]. ORGANIC LETTERS, 2006, 8 (05) : 899 - 902
  • [29] A facile access to 2-ethynyl-1,4-dihydropyridines via Hantzsch three-component reaction
    Szemes, F
    Marchalín, T
    Prónayová, N
    Szemes, F
    Daïch, A
    [J]. HETEROCYCLES, 2003, 59 (02) : 779 - 783
  • [30] One-pot synthesis of 4-aryl-1,4-dihydropyridines in water
    Shi, DQ
    Mou, J
    Zhuang, QY
    Wang, XS
    Tu, SJ
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (09) : 1042 - 1044
12345