Reaction of chloropyridazin-3(2H)-ones with iodide. Part I. A mechanistic study

G. Krajsovszky, L. Károlyházy, Zs Riedl, A. Csámpai, P. Dunkel, Á Lernyei, B. Dajka-Halász, Gy Hajós, P. Mátyus

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

In this communication we describe the reactions of 4-chloro-, 5-chloro-, and 4,5-dichloropyridazin-3(2H)-ones with 57% hydrogen iodide or sodium iodide in dimethyl formamide to afford iodopyridazin-3(2H)-ones via nucleophilic substitution followed by hydrodeiodination. The constitution of each product was proven by 1H, 13C and 15N NMR spectroscopic investigations. The mechanism proposal is based on density functional theory calculations on intermediates possibly involved in these transformations.

Original languageEnglish
Pages (from-to)235-243
Number of pages9
JournalJournal of Molecular Structure: THEOCHEM
Volume713
Issue number1-3
DOIs
Publication statusPublished - Jan 14 2005

Keywords

  • Dehalogenation
  • Density functional theory
  • Halopyridazin-3(2H)-ones
  • N NMR
  • Nucleophilic substitution
  • Regiochemistry
  • Steric buttressing

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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