Facile and Diastereoselective Arylation of the Privileged 1,4-Dihydroisoquinolin-3(2H)-one Scaffold

Submitting author affiliation:
Saint Petersburg State University, Peterhof, Russian Federation

Beilstein Arch. 2022, 202250. https://doi.org/10.3762/bxiv.2022.50.v1

Published 20 Jun 2022

cc-by Logo


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

Supporting Information

Format: DOCX Size: 14.7 MB   Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Dar'in, D.; Kantin, G.; Bunev, A.; Krasavin, M. Beilstein Arch. 2022, 202250. doi:10.3762/bxiv.2022.50.v1

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.