Synthesis of 1‐(4‐substituted)benzyl‐6‐hydroxyisoquinolines with potential activity on NA+,K+‐atpase
- 1 December 1993
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 30 (6) , 1581-1591
- https://doi.org/10.1002/jhet.5570300622
Abstract
The synthesis of 1‐(4‐substituted)benzyl‐6‐hydroxyisoquinolines, to be evaluated in the displacement of the specific 3H‐ouabain binding to Na+,K+‐ATPase, is described. The key step involved a cyclization to the isoquinoline ring under Pictet‐Gams conditions which was best performed with the 6‐hydroxy group protected as the benzyl ether. When an unsaturated ester group was present in position 4 of the 1‐benzyl group, this was best introduced before the cyclization step, since the IIeck reaction on 1‐(4‐bromobenzyl)‐6‐hydroxyisoquinoline (8) with acrylic acid derivatives was not successful in all cases.Keywords
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