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
收藏
页码：602 / 606
页数：5
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