The Preparation of Substituted Pyrazoles from β,β-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process

被引：22

作者：

Beltran-Rodil, Sandra ^{[1
]}

Edwards, Michael G. ^{[1
]}

Pugh, David. S. ^{[1
]}

Reid, Mark ^{[1
]}

Taylor, Richard J. K. ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

SYNLETT | 2010年 / 04期

基金：

英国工程与自然科学研究理事会;

关键词：

tandem oxidation process; TOP; beta; beta-dibromo-enones; 1,3,5-trisubstituted pyrazoles; Suzuki-Miyaura; ONE-POT CONVERSION; OXIDATION PROCESSES; MANGANESE-DIOXIDE; KETONES; 1,1-DIBROMO-1-ALKENES; DERIVATIVES; ALKYNES;

D O I：

10.1055/s-0029-1218521

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two consecutive tandem processes are described for the regioselective, two-step synthesis of 1,3,5-trisubstituted pyrazoles from alpha-hydroxyketones. The first, a tandem MnO2-mediated oxidation/Ramirez olefination reaction, provides a facile route to beta,beta-dibromo-enones. These valuable 1,3-dicarbonyl synthons can then be converted into 1,3,5-trisubstituted pyrazoles via a second tandem hydrazine condensation/Suzuki-Miyaura cross-coupling reaction. Using these procedures, a range of aryl and alkyl alpha-hydroxyketones have been transformed regioselectively into 1,3,5-trisubstituted pyrazoles.

引用

页码：602 / 606

页数：5

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