Synthesis and structure of planar chiral ferroceno[d]pyridazinones, the first representatives of a novel class of fused metallocenes

Á Gyömöre, A. Csámpai

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A series of planar chiral ferroceno[d]pyridazinones was prepared by hydrazine-mediated cyclisations of (Sp)-2-formylferrocenoyl fluoride obtained in two steps from (2S,4S)-4-(methoxymethyl)-2-ferrocenyl-1,3-dioxane. Further derivatives based on the novel heterocyclic scaffold were resulted by means of the facile N-alkylation reactions carried out on the easily accessible fused product derived from the hydrazine-mediated cyclisation. Upon treatment with hydrazine (Sp)-2-formylferroce carboxylic acid, the precursor of the acid fluoride with enhanced reactivity, afforded a dimeric azine avoiding cyclisation. The spectacular difference between the experimentally observed reactivity of the bifunctional formylferrocenes was disclosed by comparative DFT analysis of the assumed hydrazone- and hydrazide intermediates with different values of LUMO energy associated with different conformation. The structures of the new compounds were established by IR and NMR spectroscopy, including HMQC, HMBC and DNOE measurements.

Original languageEnglish
Pages (from-to)1626-1631
Number of pages6
JournalJournal of Organometallic Chemistry
Volume696
Issue number8
DOIs
Publication statusPublished - Apr 15 2011

Keywords

  • Condensed ferrocene
  • DFT modelling
  • NMR spectroscopy
  • Planar chirality
  • Pyridazine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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