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

[1] Unexpected 1,2,3-triazole formation in the reaction of diethylaluminum azide with α′-amino-α,β-unsaturated ketones [J].

Adamo, I ;

Benedetti, F ;

Berti, F ;

Nardin, G ;

Norbedo, S .

TETRAHEDRON LETTERS, 2003, 44 (51) :9095-9097

[2] Alterations in skeletal muscle protein-tyrosine phosphatase activity and expression in insulin-resistant human obesity and diabetes [J].

Ahmad, F ;

Azevedo, JL ;

Cortright, R ;

Dohm, GL ;

Goldstein, BJ .

JOURNAL OF CLINICAL INVESTIGATION, 1997, 100 (02) :449-458

[3] 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

[4] 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

[5] PREPARATION AND REACTIONS OF 5-VINYLTETRAZOLE [J].

ARNOLD, C ;

THATCHER, DN .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) :1141-&

[6] Efficient syntheses of 5-aminoalkyl-1H-tetrazoles and of polyamines incorporating tetrazole rings [J].

Athanassopoulos, CM ;

Garnelis, T ;

Vahliotis, D ;

Papaioannou, D .

ORGANIC LETTERS, 2005, 7 (04) :561-564

[7] Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide [J].

Benedetti, F ;

Berti, F ;

Norbedo, S .

TETRAHEDRON LETTERS, 1998, 39 (43) :7971-7974

[8]

BERNSTEIN PR, 1987, SYNTHESIS-STUTTGART, P1133

[9] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[10]

Bosch L., 2007, ANGEW CHEM, V119, P4000

← 1 2 3 4 5 6 7 8 9 →