A convenient synthesis of 1-(4-fluorophenyl)-2-(4-pyridyl)cyclopentene from cyclopentanone

被引：3

作者：

Abu Thaher, Bassam ^{[1
]}

Koch, Pierre ^{[2
]}

Del Amo, Vicente ^{[3
]}

Knochel, Paul ^{[3
]}

Laufer, Stefan ^{[2
]}

机构：

[1] Islam Univ Gaza, Dept Chem, Fac Sci, Gaza, Israel

[2] Univ Tubingen, Inst Pharm, Dept Pharmaceut & Med Chem, D-72076 Tubingen, Germany

[3] Univ Munich, Inst Chem & Biochem, D-81377 Munich, Germany

来源：

SYNTHESIS-STUTTGART | 2008年 / 02期

关键词：

Grignard reactions; carbocycles; medicinal chemistry; neodymium salt; inhibitors;

D O I：

10.1055/s-2007-1000855

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the framework of investigating the role of pyridyl-substituted five-membered heterocycles as potential p38 mitogen-activated protein kinase inhibitors, we synthesized the disubstituted carbocyclic analogue, 1-(4-fluorophenyl)-2-(4-pyridyl)cyclopentene. A multistep synthesis of this compound starting from cyclopentanone is reported. Cyclopentanone was converted into 1-cyclopentenyl-4-fluorobenzene using a Grignard reaction. The oxidation of this product with hydrogen peroxide and formic acid gave 2(4-fluorophenyl)cyclopentanone. This ketone was activated using a neodymium salt (NdCl3 center dot 2LiCl) and subsequently reacted with a complexed Grignard reagent (pyMgCl center dot LiCl) to give the corresponding cyclopentanol derivative. Finally, dehydration of the latter alcohol led to the title compound.

引用

收藏

页码：225 / 228

页数：4

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