Synthesis of 8,9-dialkoxybenzodiazepines and 7,8-dialkoxyisoquinolines

László Pongó, Béla Ágai, Ferenc Faigl, József Reiter, Gyula Simig

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

o-Aroylarylacetone type 1,5-diketone derivatives (5, 6) were synthesised from arylacetones (1) protected as 1,3-dioxolanes (4) through directed ortho lithiation followed by acylation with aroyl chlorides. 8,9-Dialkoxy-2,3- benzodiazepines 9 were obtained by cyclisation of diketones 6 with hydrazine. The reaction of diketones 6 with ammonia gave 7,8-dialkoxyisoquinolines 11. Reaction of ketals 5 with hydrazine hydrochloride and hydroxylamine hydrochloride afforded N-amino-7,8-dialkoxyisoquinolinium chlorides (10) and 7,8-dialkoxyisoquinolinium oxides (12), respectively.

Original languageEnglish
Pages (from-to)1539-1547
Number of pages9
JournalJournal of Heterocyclic Chemistry
Volume43
Issue number6
DOIs
Publication statusPublished - Jan 1 2006

ASJC Scopus subject areas

  • Organic Chemistry

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