Task-Specific Ionic Liquid as Reagent and Reaction Medium for the One-Pot Horner-Wadsworth-Emmons-Type Reaction Under Microwave Irradiation

被引：25
|
作者：
Valizadeh, Hassan [1 ]
Shockravi, Abbas [2 ]
机构：
[1] Azarbaijan Univ Tarbiat Moallem, Dept Chem, Fac Sci, Tabriz, Iran
[2] Univ Tarbiat Moallem, Fac Chem, Tehran, Iran
来源：
SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 24期
关键词：
Coumarin; Horner-Wadsworth-Emmons reaction; microwave; task-specific ionic liquid; SOLVENT-FREE CONDITIONS; WITTIG REACTIONS; COUMARIN DERIVATIVES; ROOM-TEMPERATURE; AROMATIC-COMPOUNDS; CATALYTIC-SYSTEMS; REUSABLE CATALYST; EFFICIENT; IL-OPPH2; ALCOHOLS;
D O I：
10.1080/00397910902898650
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A task-specific imidazolium-based phosphinite ionic liquid (IL-OPPh2) was used as the dual solvent-reagent for the synthesis of E-cinamates and coumarin derivatives via the one-pot Horner-Wadsworth-Emmons-type reaction. The ionic liquid containing its corresponding phosphinite moiety was reacted with a-chloro esters and benzaldehyde or salicylaldehyde derivatives in the presence of sodium methoxide under microwave irradiation to produce the related E-cinamates or coumarins, respectively. The satisfactory results were obtained with good yields, short reaction time, and simple experimental procedure.
引用
收藏
页码：4341 / 4349
页数：9
相关论文
共 50 条
  • [1] One-pot Green Procedure for the Mannich Reaction Catalyzed by a Task-specific Ionic Liquid
    Zhao, Guozheng
    Lu, Ming
    CHIANG MAI JOURNAL OF SCIENCE, 2012, 39 (01): : 49 - 58
  • [2] One-pot fluorine-18 Horner Wadsworth Emmons reaction as a platform for labelling biomolecules
    James, Shelly
    Blecha, Joseph
    Beasley, Jonathon
    Kraus, George
    Nilsen-Hamilton, Marit
    VanBrocklin, Henry
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2013, 56 : S175 - S175
  • [3] Development of Manufacturing Processes for the Carboxylic Acid Key Intermediate of Lusutrombopag: One-Pot Reaction Process of Formylation and the Horner-Wadsworth-Emmons Reaction
    Matsuura, Takaharu
    Sato, Yusuke
    Nishino, Yutaka
    Komurasaki, Tadafumi
    Imamura, Yoshiaki
    Kakinuma, Makoto
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2020, 24 (11) : 2651 - 2656
  • [4] Novel One-pot Three-component Coupling Reaction with Trimethylsilylmethylphosphonate, Acyl Fluoride, and Aldehyde through the Horner-Wadsworth-Emmons Reaction
    Umezawa, Taiki
    Seino, Tomoya
    Matsuda, Fuyuhiko
    ORGANIC LETTERS, 2012, 14 (16) : 4206 - 4209
  • [5] One-Pot O2-Oxidation and the Horner-Wadsworth-Emmons Reaction of Primary Alcohols for the Synthesis of (Z)-α,β-Unsaturated Esters
    Ando, Kaori
    Takaba, Chika
    Kodama, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 9723 - 9728
  • [6] Task-specific ionic liquid as base, ligand and reaction medium for the palladium-catalyzed Heck reaction
    Wang, Lei
    Li, Hongji
    Li, Pinhua
    TETRAHEDRON, 2009, 65 (01) : 364 - 368
  • [7] One-pot green procedure for Biginelli reaction catalyzed by novel task-specific room-temperature ionic liquids
    Dong, Fang
    Jun, Luo
    Xinli, Zhou
    Zhiwen, Ye
    Zuliang, Liu
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 274 (1-2) : 208 - 211
  • [8] Task-specific ionic liquid as a base catalyst and a reaction medium for Michael addition reactions
    Akselrod, Kristina
    Manchanayakage, Renuka
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [9] One-pot diazo coupling reaction under microwave irradiation in the absence of solvent
    Jin, J
    Wen, Z
    Long, J
    Wang, YM
    Matsuura, T
    Meng, JB
    SYNTHETIC COMMUNICATIONS, 2000, 30 (05) : 829 - 834
  • [10] Efficient one-pot synthesis of 1-chlorovinyl p-tolyl sulfoxides from aldehydes and ketones by the Horner-Wadsworth-Emmons reaction
    Kimura, Tsutomu
    Kobayashi, Gen
    Ijima, Shiori
    Saito, Sae
    Imafuji, Aki
    Satoh, Tsuyoshi
    HETEROATOM CHEMISTRY, 2017, 28 (05)
12345