Regioselective One-Step Synthesis of Pyrazoles from Alkynes and N-Tosylhydrazones: [3+2] Dipolar Cycloaddition/[1,5] Sigmatropic Rearrangement Cascade

被引：106

作者：

Carmen Perez-Aguilar, M. ^{[1
]}

Valdes, Carlos ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 28期

关键词：

alkyne; heterocycles; hydrazones; rearrangement; synthetic methods; CROSS-COUPLING REACTIONS; THERMAL REARRANGEMENTS; EFFICIENT SYNTHESIS; TERMINAL ALKYNES; 1,3-DIPOLAR CYCLOADDITION; DIAZOCARBONYL COMPOUNDS; CARBONYL-COMPOUNDS; DIAZO-COMPOUNDS; COMPLEXES; REAGENTS;

D O I：

10.1002/anie.201301284

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rearrangement under control: A wide variety of 3,4,5- and 1,3,5-trisubstituted pyrazoles can be prepared from tosylhydrazones of ketones and terminal alkynes through the title reaction sequence (see scheme; Ts=4-toluenesulfonyl). The rearrangement, and therefore, the regioselectivity of the reaction is controlled by the nature of the substituents of the tosylhydrazone. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7219 / 7223

页数：5

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