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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 44期

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

页码：8440 / 8444

页数：5

共 87 条

[21] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions [J].

Cobb, AJA ;

Shaw, DM ;

Longbottom, DA ;

Gold, JB ;

Ley, SV .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :84-96

[22]

Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[23] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[24]

Demko Z. P., 2002, ANGEW CHEM, V114, P2214

[25]

Demko ZP, 2002, ANGEW CHEM INT EDIT, V41, P2110, DOI 10.1002/1521-3773(20020617)41:12<2110::AID-ANIE2110>3.0.CO

[26]

2-7

[27] Preparation of 5-substituted 1H-tetrazoles from nitriles in water [J].

Demko, ZP ;

Sharpless, KB .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7945-7950

[28]

Dimroth O, 1910, BER DTSCH CHEM GES, V43, P2219

[29] 3 SYNTHETIC ROUTES TO A STERICALLY HINDERED TETRAZOLE - A NEW ONE-STEP MILD CONVERSION OF AN AMIDE INTO A TETRAZOLE [J].

DUNCIA, JV ;

PIERCE, ME ;

SANTELLA, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2395-2400

[30] Synthesis of fused tetrazole derivatives via a tandem cycloaddition and N-allylation reaction and parallel synthesis of fused tetrazole amines [J].

Ek, F ;

Manner, S ;

Wistrand, LG ;

Frejd, T .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1346-1352

← 1 2 3 4 5 6 7 8 9 →