Synthesis, IR-, NMR-, DFT and X-ray study of ferrocenyl heterocycles from thiosemicarbazones. Part 21

Study on ferrocenes

Balázs Fábián, Veronika Kudar, A. Csámpai, Tibor Zs Nagy, P. Sohár

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Cyclization reactions of the thiosemicarbazones of formyl- and acetylferrocene and their S-methyl derivatives with DMAD afforded novel ferrocenyl-hydrazono-substituted thiazolones, one-one dimethylthiazole-4,5-dicarboxylate and 1,3-thiazin-4-one, N-ferrocenylimino-pyrimidones/imidazolones, one intermediate β-adduct and via oxidative cyclization, a ferrocenyl-1,2,4-triazole. Ring isomerization of 1,3-thiazin-4-ones to a 1,3-thiazolones was detected. The structure of the new compounds was established by IR and NMR spectroscopy, including HMQC, HMBC and DEPT measurements and supported with GIAO NMR calculations and controlled also synthetically by phase-transfer methylation. For three compounds the stereostructure was also proved by X-ray diffraction.

Original languageEnglish
Pages (from-to)5621-5632
Number of pages12
JournalJournal of Organometallic Chemistry
Volume692
Issue number25
DOIs
Publication statusPublished - Dec 1 2007

Fingerprint

ferrocenes
Thiosemicarbazones
Cyclization
Discrete Fourier transforms
Pyrimidinones
Nuclear magnetic resonance
X-Rays
X rays
nuclear magnetic resonance
methylation
Methylation
synthesis
Isomerization
X-Ray Diffraction
isomerization
Nuclear magnetic resonance spectroscopy
adducts
Infrared spectroscopy
x rays
Magnetic Resonance Spectroscopy

Keywords

  • DFT calculations
  • Ferrocene
  • Heterocycles
  • NMR spectroscopy
  • S-O and S-N close contact
  • X-ray diffraction

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Materials Science (miscellaneous)
  • Chemical Engineering (miscellaneous)

Cite this

Synthesis, IR-, NMR-, DFT and X-ray study of ferrocenyl heterocycles from thiosemicarbazones. Part 21 : Study on ferrocenes. / Fábián, Balázs; Kudar, Veronika; Csámpai, A.; Nagy, Tibor Zs; Sohár, P.

In: Journal of Organometallic Chemistry, Vol. 692, No. 25, 01.12.2007, p. 5621-5632.

Research output: Contribution to journalArticle

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