Title
Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Cambridge ,
Subject
Chemistry
Source (journal)
Organic and biomolecular chemistry. - Cambridge, 2003, currens
Volume/pages
9(2011) :2 , p. 538-548
ISSN
1477-0520
1477-0539
1477-0520
ISI
000285749800031
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
1,2-Disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones are prepared for the first time through an activated PictetSpengler 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.
E-info
https://repository.uantwerpen.be/docman/iruaauth/b89fb8/5cf137f4b4d.pdf
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