1,3-dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles

被引:155
作者
Aureggi, Valentina [1 ]
Sedelmeier, Gottfried [1 ]
机构
[1] Novartis Pharma AG, Chem & Analyt Dev, CH-4057 Basel, Switzerland
关键词
azides; cycloaddition; nitriles; sartans; tetrazoles;
D O I
10.1002/anie.200701045
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cheap and safe: Conventional methods to prepare tetrazoles employ dangerous, toxic reagents. A new route to these heterocycles (see scheme) uses inexpensive and nontoxic dialkyl aluminum azides. The cycloaddition occurs under mild conditions and tolerates a variety of functional groups. The low cost and ecocompatibility make this process attractive for large-scale preparation. (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:8440 / 8444
页数:5
相关论文
共 87 条
[61]  
Miyata Y., 2005, SCI TECHNOL ENERG MA, V66, P233
[62]   Diastereo- and enantioselective synthesis of nitroso Diels-Alder-type bicycloketones using dienamine: Mechanistic insight into sequential nitroso aldol/Michael reaction and application for optically pure 1-amino-3,4-diol synthesis [J].
Momiyama, Norie ;
Yamamoto, Yuhei ;
Yamamoto, Hisashi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1190-1195
[63]   STUDIES ON ANTIANAPHYLACTIC AGENTS .5. SYNTHESIS OF 3-(1H-TETRAZOL-5-YL)CHROMONES, A NEW SERIES OF ANTIALLERGIC SUBSTANCES [J].
NOHARA, A ;
KURIKI, H ;
SAIJO, T ;
SUGIHARA, H ;
KANNO, M ;
SANNO, Y .
JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (01) :141-145
[64]   Enamine-based organocatalysis with proline and diamines: The development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-Alder reactions [J].
Notz, W ;
Tanaka, F ;
Barbas, CF .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :580-591
[65]   Noncovalent interactions between tetrazole and an N,N′-diethyl-substituted benzamidine [J].
Peters, L ;
Fröhlich, R ;
Boyd, ASF ;
Kraft, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10) :3291-3298
[66]   ORGANOALUMINUM CHEMISTRY .3. DIETHYLALUMINUM AZIDE [J].
PRINCE, MI ;
WEISS, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1966, 5 (06) :584-&
[67]   ONE-STEP CONVERSION OF ESTERS TO ACYL AZIDES USING DIETHYLALUMINUM AZIDE [J].
RAWAL, VH ;
ZHONG, HM .
TETRAHEDRON LETTERS, 1994, 35 (28) :4947-4950
[68]  
RODER N, 1974, CHIMIA, V28, P349
[69]   ZUR ACYLIERUNG VON 5-ARYL-TETRAZOLEN - EIN DUPLIKATIONSVERFAHREN ZUR DARSTELLUNG VON POLYARYLEN [J].
SAUER, J ;
HUISGEN, R ;
STURM, HJ .
TETRAHEDRON, 1960, 11 (04) :241-251
[70]   Safe and fast tetrazole formation in ionic liquids [J].
Schmidt, Boris ;
Meid, Daniela ;
Kieser, Daniel .
TETRAHEDRON, 2007, 63 (02) :492-496