"On Water" Nucleophilic Addition of Pyrazolones to Trifluoromethyl Ketones

被引:1
作者
Luo, Liang [1 ]
Cao, Xiaomei [1 ]
Lai, Guowei [1 ]
Liu, Jinxiang [1 ]
Luo, Haiqing [1 ]
Lu, Dongliang [1 ]
Zhang, Yong [1 ]
机构
[1] Gannan Normal Univ, Key Lab Organopharmaceut Chem, Ganzhou 341000, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
on water" reaction; nucleophilic addition; pyrazolone; trifluoromethyl ketone; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; ORGANIC-REACTIONS; CATALYST-FREE; DIFLUOROMETHYLATED ARENES; MICHAEL ADDITION; FACILE SYNTHESIS; ALDOL REACTION; ON-WATER; FLUORINE; CONSTRUCTION;
D O I
10.6023/cjoc201910038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A green and efficient nucleophilic addition reaction of trifluoromethyl ketone with pyrazolone was developed under "on water" conditions, affording pyrazolone substituted tertiary trifluoromethyl alcohols in high yields. The advantages of being catalyst-free, column chromatography-free, environmentally benign and easy workup make it a promising method for preparation of a variety of pyrazolone substituted tertiary trifluoromethyl alcohols.
引用
收藏
页码:1323 / 1330
页数:8
相关论文
共 88 条
[1]  
Anastas PT, 1998, GREEN CHEM FRONTIERS
[2]  
[Anonymous], 2015, GREEN CHEM
[3]   Review: biologically active pyrazole derivatives [J].
Ansari, Anam ;
Ali, Abad ;
Asif, Mohd ;
Shamsuzzaman .
NEW JOURNAL OF CHEMISTRY, 2017, 41 (01) :16-41
[4]   Stereoselective Synthesis of 3,3'-Bisindolines by Organocatalytic Michael Additions of Fluorooxindole Enolates to Isatylidene Malononitriles in Aqueous Solution [J].
Balaraman, Kaluvu ;
Ding, Ransheng ;
Wolf, Christian .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (23) :4165-4169
[5]   Cyclization of some carbothioamide derivatives containing antipyrine and triazole moieties and investigation of their antimicrobial activities [J].
Bayrak, Hacer ;
Demirbas, Ahmet ;
Demirbas, Neslihan ;
Karaoglu, Sengul Alpay .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) :4726-4732
[6]   Synthesis and antimicrobial activity of some new heterocycles incorporating antipyrine moiety [J].
Bondock, Samir ;
Rabie, Ramy ;
Etman, Hassan A. ;
Fadda, Ahmed A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (10) :2122-2129
[7]   Organic synthesis reactions on-water at the organic-liquid water interface [J].
Butler, Richard N. ;
Coyne, Anthony G. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (42) :9945-9960
[8]   Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides [J].
Cook, Andrea M. ;
Wolf, Christian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (08) :2925-2929
[9]   Unprecedented Nucleophilic Additions of Highly Polar Organometallic Compounds to Imines and Nitriles Using Water as a Non-Innocent Reaction Medium [J].
Dilauro, Giuseppe ;
Dell' Aera, Marzia ;
Vitale, Paola ;
Capriati, Vito ;
Perna, Filippo Maria .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (34) :10200-10203
[10]   Organocatalytic Asymmetric Benzylation and Aldol-Hemiacetalization of α,β-Unsaturated Trifluoromethyl Ketones: Efficient Enantioselective Construction of 3,4-Dihydroisocoumarins [J].
Duan, Jindian ;
Cheng, Yuyu ;
Cheng, Jing ;
Li, Rou ;
Li, Pengfei .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (03) :519-523