Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 2, Pages 538-548Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00391c
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Funding
- Research Foundation - Flanders (FWO-Vlaanderen)
- Vrije Universiteit Brussel (HOA)
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1,2-Disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones are prepared for the first time through an activated Pictet-Spengler reaction of the corresponding imines of 2-(1,4-dimethoxynaphth-2-yl)ethylamine in the presence of an acyl chloride and AlCl3 followed by an oxidation with silver(II) oxide in nitric acid. Depending on the reaction conditions the N-trichloroacetyl protecting group could be cleaved off, converted to an N-methoxycarbonyl group or transformed to an N-(2-oxoacetamide) moiety. The synthesized 1,2-disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones constitute a new class of quinones, which has not been reported yet.
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