A practical multigram-scale method for the green synthesis of 5-substituted-1H-tetrazoles in deep eutectic solvent

被引:45
作者
Xiong, Xingquan [1 ]
Yi, Chao [1 ]
Liao, Xu [1 ]
Lai, Shilin [1 ]
机构
[1] Univ Huaqiao, Coll Mat Sci & Engn, Xiamen 361021, Peoples R China
基金
中国国家自然科学基金;
关键词
5-Substituted-1H-tetrazoles; Aldehydes; One-pot synthesis; Deep eutectic solvent; Green chemistry; 5-SUBSTITUTED; 1H-TETRAZOLES; 3+2 CYCLOADDITION; RECYCLABLE CATALYST; EFFICIENT SYNTHESIS; REUSABLE CATALYST; N-ARYLATION; NITRILES; NANOPARTICLES; COMPLEX; HETEROCYCLES;
D O I
10.1016/j.tetlet.2018.12.037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 5-substituted-1H-tetrazoles have been efficiently synthesized in moderate to excellent yields (68-90%) under mild reaction conditions by combining aryl aldehydes, hydroxylamine hydrochloride with sodium azide in the presence of catalytic amount of Cu(OAc)(2) in deep eutectic solvent (DES). The new synthetic method has many advantages, such as high conversion, green reaction medium, easy work-up, low cost, and environment friendly. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:402 / 406
页数:5
相关论文
共 53 条
[1]   Glycerol eutectics as sustainable solvent systems [J].
Abbott, Andrew P. ;
Harris, Robert C. ;
Ryder, Karl S. ;
D'Agostino, Carmine ;
Gladden, Lynn F. ;
Mantle, Mick D. .
GREEN CHEMISTRY, 2011, 13 (01) :82-90
[2]   Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids [J].
Abbott, AP ;
Boothby, D ;
Capper, G ;
Davies, DL ;
Rasheed, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :9142-9147
[3]   Novel solvent properties of choline chloride/urea mixtures [J].
Abbott, AP ;
Capper, G ;
Davies, DL ;
Rasheed, RK ;
Tambyrajah, V .
CHEMICAL COMMUNICATIONS, 2003, (01) :70-71
[4]   Multi-component one-pot reaction of aldehyde, hydroxylamine and sodium azide catalyzed by Cu-MCM-41 nanoparticles: a novel method for the synthesis of 5-substituted 1H-tetrazole derivatives [J].
Abdollahi-Alibeik, Mohammad ;
Moaddeli, Ali .
NEW JOURNAL OF CHEMISTRY, 2015, 39 (03) :2116-2122
[5]  
Ahmet O., 2015, LETT DRUG DES DISCOV, V12, P687
[6]  
Amaroju S., 2016, CHEMISTRYSELECT, V1, P1705
[7]  
[Anonymous], 2002, J CHEM SOC P1
[8]   Highly Efficient Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by Cu-Zn Alloy Nanopowder, Conversion into 1,5-and 2,5-Disubstituted Tetrazoles, and Synthesis and NMR Studies of New Tetrazolium Ionic Liquids [J].
Aridoss, Gopalakrishnan ;
Laali, Kenneth K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (31) :6343-6355
[9]   1,3-dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles [J].
Aureggi, Valentina ;
Sedelmeier, Gottfried .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (44) :8440-8444
[10]   Highly efficient three-component synthesis of 5-substituted-1H-tetrazoles from aldehydes, hydroxylamine, and tetrabutylammonium azide using doped nano-sized copper(I) oxide (Cu2O) on melamine-formaldehyde resin [J].
Behrouz, Somayeh .
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2017, 21 (02) :220-228