A practically convenient and streamlined protocol for trans-diastereoselective introduction of an aryl substituent at position 4 of 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 investigation as anticancer cytotoxic agents.
Keywords: heterocyclic diazo compounds; Regitz diazo transfer; 1,4-dihydroisoquinol-3-one; triflic acid; hydroarylation
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Dar'in, D.; Kantin, G.; Bunev, A.; Krasavin, M. Beilstein Arch. 2022, 202250. doi:10.3762/bxiv.2022.50.v1
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