Preparation of heterocyclic dications from substituted phthalazinones

A. Csámpai, K. Körmendy, T. Sohár, J. Császár, F. Ruff

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Abstract

Using perchloric acid 2-(ω-hydroxyalkyl)-4-(ω)'-hydroxyalkyl~ amino)phthalazinones and their 6,7-dimethoxy derivatives were converted into tetracyclic dications containing both iminoether and amidine moieties The 2-(4~hydroxyt)utyl) chain avoided the formation of seven-membered ring with either isomerisation or degradation involving cleavage of C-N bond assisted by neighbouring group participation of the hydroxyl group. The sequence of ring closures depends on the ring substituents and the lengths of side chains. The reaction mechanism is also influenced by the site of the protonation. The structures of the new tetracycles were proved by 1H- and 13C-nmr spectroscopy.

Original languageEnglish
Pages (from-to)6895-6902
Number of pages8
JournalTetrahedron
Volume46
Issue number19
DOIs
Publication statusPublished - 1990

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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