Beilstein J. Org. Chem.2022,18, 1070–1078, doi:10.3762/bjoc.18.109
, Russian Federation 10.3762/bjoc.18.109 Abstract 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 Regitzdiazotransfer onto
cytotoxic agents.
Keywords: 1,4-dihydroisoquinol-3-one; heterocyclic diazo compounds; hydroarylation; Regitzdiazotransfer; triflic acid; Introduction
Besides being derivatives of (or a precursor to) the 1,2,3,4-tetrahydroisoquinoline core which itself bears a special significance from the standpoint of
in the literature. While pondering possible solutions to fill this void, we drew inspiration in our recent success achieving direct Brønsted acid-catalyzed C-arylation of 4-diazo-isoquinoline-1,3-diones 7 [9] which are, in turn, obtainable via the Regitzdiazotransfer reaction onto readily available
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Graphical Abstract
Figure 1:
Diverse bioactive compounds based on the privileged 1,4-DHIQ scaffold.