Synthesis of 2-ferrocenylidene-4-cyclopentene-1,3-diones


Zora M., KÖKTÜRK M., Eralp T.

TETRAHEDRON, vol.62, no.44, pp.10344-10351, 2006 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 62 Issue: 44
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tet.2006.08.078
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.10344-10351
  • Keywords: ferrocenylidenecyclopentenediones, ferrocenyl quinones, alkynylcyclobutenones, cyclobutenediones, cyclobutenols, rearrangement, radicals, ESTROGEN-RECEPTOR MODULATORS, TYROSINE KINASE INHIBITOR, LINDERA-ERYTHROCARPA-MAKINO, RADICAL-STABILIZING ABILITY, LOW MITOCHONDRIAL TOXICITY, ACTIVITY IN-VITRO, ANTIMALARIAL ACTIVITY, ANTITUMOR 2-HYDROXYARYLIDENE-4-CYCLOPENTENE-1,3-DIONE, FERROCENE-CHLOROQUINE, FERRICENIUM COMPLEXES

Abstract

A squarate-based synthesis of 2-ferrocenylidene-4-cyclopentene-1,3-diones is described. When refluxed in dioxane at 100 degrees C, heated with silica gel as a solvent free grinded solid mixture at 125 degrees C or stirred with silica gel in ethyl acetate at room temperature, 4-ferrocenylethynyl-4-hydroxy-2-cyclobutenones, prepared from ethynylferrocene and 3-cyclobutene-1,2-diones, afforded 2-ferrocenylidene-4-cyclopentene-1,3-diones as the major or single product of the reaction. In some cases, ferrocenyl quinones also resulted from these reactions as the minor products. The major or exclusive formation of 2-ferrocenylidene-4-cyclopentene-1,3-diones is attributed to the radical-stabilizing ability of the ferrocenyl group.. (c) 2006 Elsevier Ltd. All rights reserved.