SYNTHESIS OF 1-FUNCTIONALIZED-6-HYDROXY-4-METHYLNAPHTHO[2,3-G]ISOQUINOLINE-5,12-QUINONES AND 1-FUNCTIONALIZED-6,11-DIHYDROXY-4-METHYLNAPHTHO[2,3-G]ISOQUINOLINE-5,12-QUINONES

被引：10

作者：

CROISYDELCEY, M ^{[1
]}

BISAGNI, E ^{[1
]}

HUEL, C ^{[1
]}

ZILBERFARB, D ^{[1
]}

CROISY, A ^{[1
]}

机构：

[1] INST CURIE,BIOL SECT,INSERM,U219,F-91405 ORSAY,FRANCE

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 01期

关键词：

D O I：

10.1002/jhet.5570280112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using 2-methoxy- and 2,5-dimethoxyacetophenone 8a and 8b as starting materials, 1-chloro-4-methylisoquinoline-5,8-quinone (6) and its 6-bromo derivative 7 were obtained via multistep sequences. Whereas Diels-Alder condensation of the former compound with homophthalic anhydride (22) led to a mixture of the two possible isomers: 1-chloro-11-hydroxy-4-methylnaphtho[2,3-g]isoquinoline-5,12-quinone (23) and 1-chloro-6-hydroxy-4-methylnaphtho[2,3-g]isoquinoline-5,12-quinone (24), this last tetracyclic chloroquinone was specifically obtained from 6-bromo-1-chloro-4-methylisoquinoline?? -5,8-quinone (7) and homophthalic anhydride. The 6,11-dihydroxy derivative was then prepared by ammonium nitrate oxidation or photochemically by cycloaddition of benzocyclobutenedione (28) and 1-chloro-4-methylisoquinoline-5,8-quinone (6). Chloro compounds were easily substituted by diamines to provide corresponding 1-aminosubstituted hydroxy tetracyclic quinones.

引用

页码：65 / 71

页数：7

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