Chain length dependent reactivity of 2-(ω-hydroxyalkyl)-4-(ω-hydroxyalkylamino)phthalazin-1(2h)-ones in azeotropic hydrobromic acid

A. CsXmpai, K. Körmendy, F. Ruff

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

In boiling 48% HBr conversions of title compounds (5a-f) resulted in 2-(ω)-bromoalkyl)-4-(2-hydroxyethylamino)-phthalazinones 8a,c, angular tricycles 7a,c-f and the 14a tricyclic dione, respectively, depending on the lengths of the side chains and the reaction time applied. The large difference between the reactivities of 4-(2-hydroxyethylamino)- and 4-(3-hydroxypropylamino) homologues in the exchange OH → Br was interpreted on the basis of the relative OH-basicities in the N3-protonated molecules. The proposed mechanism for the conversion to 14a involving a Smiles-type rearrangement was supported by additional experiments with 4-amino-2-(ω-hydroxyalkyl)-phthalazinones 15a,b.

Original languageEnglish
Pages (from-to)4457-4464
Number of pages8
JournalTetrahedron
Volume47
Issue number25
DOIs
Publication statusPublished - 1991

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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