Preparation and structure of bicycloalkane-condensed aryldiaziridines accompanied by pyrimidines

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Abstract

Di-exo- and di-endo-2-aminonorbomane/enemethanamines 1-3, di-exo-oxanorbomene derivative 4 and cis-cyclohexane and trans-4-cyclohexene analogues 5, 6 were reacted with p-chlorobenzaldehyde in the presence of N-bromosuccinimide in dichloromethane. Via the reactions of 1-6, condensed diaziridines 7-12 accompanied by pyrimidine derivatives 13-16 were prepared after isolation with column chromatography. The mechanisms proposed for alternative transformations were supported by DFT calculations. The structures of the new compounds were proved by IR and NMR spectroscopy and, for 7, 9 and 12, also by means of X-ray crystallography.

Original languageEnglish
Pages (from-to)1315-1326
Number of pages12
JournalHeterocycles
Volume71
Issue number6
Publication statusPublished - jún. 1 2007

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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