Tungstates: Novel heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles

被引:76
作者
He, Jinghui [1 ]
Li, Baojun [1 ]
Chen, Fasheng [1 ]
Xu, Zheng [1 ]
Yin, Gui [1 ]
机构
[1] Nanjing Univ, State Key Lab Coordinat Chem, Sch Chem & Engn, Nanjing 210093, Jiangsu, Peoples R China
关键词
Tetrazoles; Tungstate; BaWO4; 2+3]-Cycloaddition; Heterogeneous catalyst; TETRAZOLE FORMATION; EFFICIENT SYNTHESIS; NITRILES; AZIDE; CHEMISTRY; SURFACE; OXYGEN;
D O I
10.1016/j.molcata.2009.01.037
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
Most heterogeneous Catalysts utilized for the formation of 5-substituted 1H-tetrazoles contain zinc as the metal core at the catalytically active site. In this paper, we report that the tungstate MWO4 (M = Ba, Ca, Zn, Cd, Cu. Na, H) can catalyze the [2+3] cycloaddition reaction of nitriles with sodium azide to produce 5-substituted 1H-tetrazoles in DMF The catalyst is very efficient, affording good yield of aromatic nitriles and can be reused for several cycles. The mono- and di-addition products from dicyanobenzene can be selectively synthesized, which is a development being reported for the first time. The mechanism of the catalysis may originate from the nitrile group coordinating With the unsaturated W atoms, formed by oxygen vacancies on the surface of solid tungstates. (c) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:135 / 138
页数:4
相关论文
共 29 条
[1]   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
[2]  
Butler R.N., 1996, Comprehensive Heterocyclic Chemistry II, V4
[3]   ACTIVATION OF SILICON HYDROGEN, SILICON OXYGEN, SILICON NITROGEN BONDS IN HETEROGENEOUS PHASE - SOME NEW METHODS IN ORGANIC-SYNTHESIS [J].
CORRIU, RJP ;
PERZ, R ;
REYE, C .
TETRAHEDRON, 1983, 39 (06) :999-1009
[4]   tris(2-perfluorohexylethyl) tin azide:: A new reagent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous organic liquid-liquid extraction [J].
Curran, DP ;
Hadida, S ;
Kim, SY .
TETRAHEDRON, 1999, 55 (29) :8997-9006
[5]   An expedient route to the tetrazole analogues of α-amino acids [J].
Demko, ZP ;
Sharpless, KB .
ORGANIC LETTERS, 2002, 4 (15) :2525-2527
[6]   Preparation of 5-substituted 1H-tetrazoles from nitriles in water [J].
Demko, ZP ;
Sharpless, KB .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7945-7950
[7]  
DUNICA JV, 1991, J ORG CHEM, V56, P2395
[8]   Electron localization determines defect formation on ceria substrates [J].
Esch, F ;
Fabris, S ;
Zhou, L ;
Montini, T ;
Africh, C ;
Fornasiero, P ;
Comelli, G ;
Rosei, R .
SCIENCE, 2005, 309 (5735) :752-755
[9]   The role of surface oxygen vacancies upon WO3 conductivity [J].
Gillet, M ;
Lemire, C ;
Gillet, E ;
Aguir, K .
SURFACE SCIENCE, 2003, 532 :519-525
[10]   Quantum chemical modeling (DFT) of active species on the V-W-O catalyst surface in various redox conditions [J].
Góra, A ;
Broclawik, E ;
Najbar, M .
COMPUTERS & CHEMISTRY, 2000, 24 (3-4) :405-410