Highly substrate selective nucleophilic amination of nitro-substituted 4-(2-hydroxyethylamino)phthalazin-1(2H)-ones

A. Szabó, M. Fuxreiter, A. Csámpai, K. Körmendy, J. Császár

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Abstract

An unexpected selectivity was observed in the aromatic displacement reaction of 4-(2-hydroxyethylamino)phthalazinones 1-3 and 7, 8 differently substituted with the leaving nitro group on the condensed benzene ring. On treatment with a series of amine and hydrazine nucleophiles, the 8-nitro isomers 1-3 were readily transformed into the corresponding aromatic amine (4-6), while the substrates carrying the nitro group at position 6 or 7 (7 and 8) remained unchanged on prolonged treatment with any of the reagents used. Application of pyridine or DMF as a solvent proved to be indispensable to successful conversions even of the 8-nitro derivatives 1-3.

Original languageEnglish
Pages (from-to)555-562
Number of pages8
JournalHeterocyclic Communications
Volume3
Issue number6
DOIs
Publication statusPublished - Jan 1 1997

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ASJC Scopus subject areas

  • Organic Chemistry

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