Synthesis, ring transformations, IR-, NMR and DFT study of heterocycles with two ferrocenyl units

Balázs Fábián, Antal Csámpai, Tibor Zs Nagy, Mátyás Czugler, Pál Sohár

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Cyclization of 1,5-bis(ferrocenylmethylidene)thiocarbonohydrazide with DMAD afforded diastereomeric dimethyl-thiazole-4,5-dicarboxylates. The cis-isomer undergoes ring opening and recyclization to a thiazolone derivative. A further thiazolone was obtained from this precursor with ethyl chloroacetate employing a bifunctional organocatalyst. Due to its propensity to dehydrogenation evidenced by DFT calculations, the studied thiocarbonohydrazide underwent oxidative cyclizations under different conditions to yield a 1,3,4-thiadiazole and a 1,2,4-triazole derivative, respectively. Thermal isomerisation of 1,3,4-thiadiazole into 1,2,4-triazole was also observed. The DMAD-mediated cyclizations of the S-metylated thiocarbonohydrazide and the 1,5-bis(ferrocenylmethylideneamino)guanidine gave 1,2,4-triazole derivatives and a 4-pyrimidone, respectively. The structure of the new compounds was established by IR and NMR spectroscopy, including HMQC, HMBC and DEPT measurements. The solid state structure of a triazole was revealed by single crystal X-ray analysis.

Original languageEnglish
Pages (from-to)3732-3741
Number of pages10
JournalJournal of Organometallic Chemistry
Volume694
Issue number23
DOIs
Publication statusPublished - Nov 1 2009

Keywords

  • DFT
  • Ferrocene
  • Heterocycles
  • NMR
  • Organocatalysis
  • Ring transformation
  • X-ray diffraction

ASJC Scopus subject areas

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

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