Rapid synthesis of 1-amidoalkyl-2-naphthols over sulfonic acid functionalized imidazolium salts

被引:225
|
作者
Zolfigol, Mohammad Ali [1 ]
Khazaei, Ardeshir [1 ]
Moosavi-Zare, Ahmad Reza [1 ]
Zare, Abdolkarim
Khakyzadeh, Vahid [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Hamadan 6517838683, Iran
关键词
Ionic liquid; Sulfonic acid functionalized imidazolium salts; beta-Naphthol; 1-Amidoalkyl-2-naphthol; Solvent-free; SOLVENT-FREE CONDITIONS; ONE-POT SYNTHESIS; CATALYST-FREE PROTOCOL; IONIC LIQUID; AMIDOALKYL NAPHTHOLS; ROOM-TEMPERATURE; EFFICIENT; CHLORIDE; ALDEHYDES; GREEN;
D O I
10.1016/j.apcata.2011.04.013
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Novel sulfonic acid functionalized imidazolium salts including 3-methyl-1-sulfonic acid imidazolium chloride {[Msim]Cl} (an ionic liquid), 1,3-disulfonic acid imidazolium chloride {[Dsim]Cl} (an ionic liquid) and 3-methyl-1-sulfonic acid imidazolium tetrachloroaluminate {[Msim]AlCl(4)} (a solid) efficiently catalyze one-pot multi-component condensation of beta-naphthol with aromatic aldehydes and amide derivatives under solvent-free conditions to afford 1-amidoalkyl-2-naphthols in excellent yields (81-96%) and in very short reaction times (1-40 min). (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:70 / 81
页数:12
相关论文
共 50 条
  • [31] Zirconocene dichloride catalyzed multi-component synthesis of 1-amidoalkyl-2-naphthols at ambient temperature
    Sharanabasappa Khanapure
    Megha Jagadale
    Rajashri Salunkhe
    Gajanan Rashinkar
    Research on Chemical Intermediates, 2016, 42 : 2075 - 2085
  • [32] Humic acid: An unexplored organocatalyst toward the synthesis of 1-amidoalkyl-2-naphthols and 1-thioamidoalkyl-2-naphthols through one-pot multi-component system
    Kundu, Tandra
    Mitra, Bijeta
    Ghosh, Pranab
    SYNTHETIC COMMUNICATIONS, 2023, 53 (19) : 1588 - 1600
  • [33] An Atom-Economic Efficient Synthesis of 1-Amidoalkyl-2-Naphthols Mediated By Hexachlorocyclotriphosphazene (HCCP) as a Novel Catalyst
    Singh, Rajesh K.
    Chaudhary, Shallu
    Prasad, D. N.
    Kumar, Sahil
    LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (10) : 846 - 850
  • [34] 1,3-Dibromo 5,5-Dimethylhydantoin (DBH) Catalyzed, Microwave-assisted Rapid Synthesis of 1-Amidoalkyl-2-naphthols
    Habibzadeh, Setareh
    Ghasemnejad-bosra, Hassan
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2012, 59 (02) : 193 - 198
  • [35] Boric acid as a mild and efficient catalyst for one-pot synthesis of 1-amidoalkyl-2-naphthols under solvent-free conditions
    Shahrisa, Aziz
    Esmati, Somayeh
    Nazari, Mahdi Gholamhosseini
    JOURNAL OF CHEMICAL SCIENCES, 2012, 124 (04) : 927 - 931
  • [36] SYNTHESIS OF BENZOXANTHENES AND 1-AMIDOALKYL-2-NAPHTHOLS USING SOLID SUPPORTED PbCl2 UNDER SOLVENT FREE CONDITION
    Patil, Vishvanath D.
    Sutar, Nagesh R.
    Patil, Ketan P.
    HETEROCYCLIC LETTERS, 2016, 6 (04): : 701 - 707
  • [37] One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by nano-BF3•SiO2
    Mirjalili, BiBi Fatemeh
    Bamoniri, Abdolhamid
    Rahmati, Leila
    ARABIAN JOURNAL OF CHEMISTRY, 2019, 12 (08) : 2216 - 2223
  • [38] Boric acid as a mild and efficient catalyst for one-pot synthesis of 1-amidoalkyl-2-naphthols under solvent-free conditions
    AZIZ SHAHRISA
    SOMAYEH ESMATI
    MAHDI GHOLAMHOSSEINI NAZARI
    Journal of Chemical Sciences, 2012, 124 : 927 - 931
  • [39] An efficient synthesis of 1-amidoalkyl-2-naphthols catalyzed by zinc oxide nanoparticles under solvent-free conditions
    Singh, Rajesh K.
    Bala, Renu
    Kumar, Sahil
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2016, 55 (03): : 381 - 386
  • [40] Homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H) as an efficient catalyst for one-pot synthesis of 1-amidoalkyl-2-naphthols
    Nasresfahani, Zahra
    Kassaee, Mohammad Zaman
    Eidi, Esmaiel
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (05) : 4720 - 4726