One-pot synthesis of 2-ferrocenyl-substituted pyridines

KARADENİZ E., ZORA M.

TETRAHEDRON LETTERS, vol.57, no.44, pp.4930-4934, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 57 Issue: 44
  • Publication Date: 2016
  • Doi Number: 10.1016/j.tetlet.2016.09.080
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4930-4934
  • Keywords: Pyridine, Ferrocene, Propargylamine, alpha,beta-Alkynic ketone, N-Propargylic beta-enaminone, Electrophilic cyclization, PROPARGYLIC BETA-ENAMINONES, AU(I)-CATALYZED 6-ENDO-DIG CYCLOISOMERIZATION, HETEROCYCLIC CARBENE ADDUCTS, PI-ELECTRON DELOCALIZATION, FERROCENYL-DERIVED LIGANDS, STRUCTURAL-CHARACTERIZATION, INTRAMOLECULAR CYCLIZATION, FACILE SYNTHESIS, FE(ETA(5)-C5H4-1-C5H4N)(2) LIGAND, N-PROPARGYLAMINOQUINONES
  • Middle East Technical University Affiliated: Yes

Abstract

A facile, one-pot method for the synthesis of 2-ferrocenylpyridines is described. When reacted with propargylamine, alpha,beta-alkynic ketones produced N-propargylic beta-enaminones in situ, which, in the presence of copper(I) chloride, underwent electrophilic cyclization to afford 2-ferrocenylpyridine derivatives in good to high yields. This cyclization was found to be general for a variety of alpha,beta-alkynic ketones and tolerated the presence of aryl groups with electron-withdrawing and electron-donating substituents. The enrichment of the pyridine core with a ferrocenyl moiety, in addition to benzoyl groups, may offer potential for the synthesis of molecules of pharmacological interest. (C) 2016 Elsevier Ltd. All rights reserved.