DOI

A practically convenient and streamlined protocol for the trans-diastereoselective introduction of an aryl substituent at position 4 of the 1,4-dihydroisoquinol-3-one (1,4-DHIQ) scaffold is presented. The protocol involves direct Regitz diazo transfer onto readily available 3(2H)-isoquinolones followed by TfOH-promoted hydroarylation by an arene molecule. Screening of the novel 1,2,4-trisubstituted 1,4-DHIQs against cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigations as anticancer cytotoxic agents.

Original languageEnglish
Pages (from-to)1070–1078
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume18
DOIs
StatePublished - 22 Aug 2022

    Scopus subject areas

  • Organic Chemistry

    Research areas

  • 1,4-dihydroisoquinol-3-one, Regitz diazo transfer, heterocyclic diazo compounds, hydroarylation, triflic acid

ID: 100705890