Safe and fast tetrazole formation in ionic liquids

被引:66
作者
Schmidt, Boris [1 ]
Meid, Daniela [1 ]
Kieser, Daniel [1 ]
机构
[1] Tech Univ Darmstadt, Clemens Schopf Inst Organ Chem & Biochem, D-64287 Darmstadt, Germany
关键词
D O I
10.1016/j.tet.2006.10.057
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The [2+3] cycloaddition of nitriles and azides is reliable for intramolecular reactions, but the hazards with volatile azides in intermolecular reactions are tremendous. Zinc catalysis in aqueous solution is a magnificent improvement, but requires the removal of the zinc salts from the acidic product. Herein, we report safe solvents featuring low vapor pressure and good solubility of NaN3. Ionic liquids based on alkylated imidazoles combined with microwave heating turned out to be a solution for the given tasks. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:492 / 496
页数:5
相关论文
共 21 条
[1]   Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides [J].
Alterman, M ;
Hallberg, A .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7984-7989
[2]   TBAF-Catalyzed synthesis of 5-substituted IH-tetrazoles under solventless conditions [J].
Amantini, D ;
Beleggia, R ;
Fringuelli, F ;
Pizzo, F ;
Vaccaro, L .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) :2896-2898
[3]  
Buehlmayer P., 1991, Patent Application, Patent No. [EP0443983.B1, 0443983]
[4]  
BUHLMAYER P, 1997, Patent No. 9730036
[5]  
Butler R.N., 1996, Comprehensive Heterocyclic Chemistry II, V4, P621
[6]  
BUTLER RN, 1996, COMPREHENSIVE HETERO, V4, P905
[7]   SYNTHESIS AND THERMOLYSIS OF IMIDAZOLE QUATERNARY-SALTS [J].
CHAN, BKM ;
CHANG, NH ;
GRIMMETT, MR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (09) :2005-2013
[8]   Preparation of 5-substituted 1H-tetrazoles from nitriles in water [J].
Demko, ZP ;
Sharpless, KB .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7945-7950
[9]   The distillation and volatility of ionic liquids [J].
Earle, MJ ;
Esperança, JMSS ;
Gilea, MA ;
Lopes, JNC ;
Rebelo, LPN ;
Magee, JW ;
Seddon, KR ;
Widegren, JA .
NATURE, 2006, 439 (7078) :831-834
[10]   5-substituted-1H-tetrazoles as carboxylic acid isosteres:: Medicinal chemistry and synthetic methods [J].
Herr, RJ .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) :3379-3393