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Title
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Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones
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Author
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Abstract
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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 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. |
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Language
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English
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Source (journal)
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Organic and biomolecular chemistry. - Cambridge, 2003, currens
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Publication
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Cambridge
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Royal Society of Chemistry
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2011
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ISSN
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1477-0520
[print]
1477-0539
[online]
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DOI
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10.1039/C0OB00391C
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Volume/pages
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9
:2
(2011)
, p. 538-548
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ISI
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000285749800031
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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