Study on ferrocenes, part 9 [1] substrate selective transformations of some ferrocenylhydrazones

Abrán, A. Csámpai, A. Kotschy, O. Barabás, P. Sohár

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13 Citations (Scopus)

Abstract

Different ferrocenyl-substituted hydrazones of heteroaryl/arylhydrazines (1a-e, 3 and 10) were reacted with dimethyl fumarate and gave two epimeric pairs of pyrazolidines (t, c-2a and t, c-2c), pyrazolines (5a, c, 6, 11), pyrazoles (8, 12) and condensed triazoles (4a, 7). On treatment with dicyanodichloroquinone (DDQ) the pyrido[2, 3-d]pyridazinyl-substituted hydrazones (1b, e) were cyclized to condensed triazoles 4b, e. The reactivity of 1a-e in the cycloaddition process and oxidation level of the products were found to be highly dependent on the temperature and on the heteroaryl/aryl group. The significant difference was explained by theoretical calculations. The structures of products were determined by IR, 1D and 2D NMR methods (including HMQC, HMBC and DNOE) and single crystal X-ray analysis.

Original languageEnglish
Pages (from-to)185-194
Number of pages10
JournalJournal of Molecular Structure
Volume569
Issue number1-3
DOIs
Publication statusPublished - Jul 19 2001

Keywords

  • Dipolar cycloaddition
  • Ferrocenylhydrazones
  • Semi-empirical calculations
  • Stereoselectivity
  • Structure determination

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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