Regioselective formation of N-alkyl-3,5-pyrazole derived ligands. A synthetic and computational study

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Abstract

New N-alkyl-3,5-pyrazole derived ligands were synthesized by reaction between 3,5-pyrazole derived ligands and the appropriate haloalkane in toluene or THF using NaOEt or NaH as base. When the precursor ligand bears a pyridyl substituent the alkylation reaction presents a large regioselectivity. Theoretical calculations have been carried out to rationalize the experimental observations. It has been shown that regioselectivity is governed by the formation of Na+-pyrazolide chelate complexes. © 2005 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)12377-12385
JournalTetrahedron
Volume61
Issue number52
DOIs
Publication statusPublished - 26 Dec 2005

Keywords

  • N-alkyl-3,5-pyrazole derived ligands
  • N-alkylation
  • Regioisomers

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