Journal of Heterocyclic Chemistry p. 1581 - 1592 (1993)
Update date:2022-08-02
Topics:
Cerri
Mauri
Mauro
Melloni
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 Piclet-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 Heck reaction on 1-(4- bromobenzyl)-6-hydroxyisoquinoline (8) with acrylic acid derivatives was not successful in all cases.
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