B. A. Thaher, P. Koch, V. D. Amo
2008
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Synthesis
Abstract
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-cy--clo-pentenyl-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 (NdCl 3 ·2LiCl) and subsequently reacted with a complexed Grignard reagent (pyMgCl·LiCl) to give the corresponding cyclopentanol derivative. Finally, dehydration of the latter alcohol led to the title compound.