Facile oxidation of fused 1,4-dimethoxybenzenes to 1,4-quinones using NBS:Fine-tuned control over bromination and oxidation reactions

Authors
Kim, DW Choi, HY Lee, KJ Chi, DY
Citation
Dw. Kim et al., Facile oxidation of fused 1,4-dimethoxybenzenes to 1,4-quinones using NBS:Fine-tuned control over bromination and oxidation reactions, ORG LETT, 3(3), 2001, pp. 445-447
Citations number
35
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
3
Year of publication
2001
Pages
445 - 447
Database
ISI
SICI code
1523-7060(20010208)3:3<445:FOOF1T>2.0.ZU;2-8
Abstract
[GRAPHICS] Fused 1,4-dimethoxybenzenes could be oxidized to benzoquinones by either di rect oxidation or demethylation-oxidation. The oxidative demethylation of 5 ,8-dimethoxy-2-methylquinoline using 1.1 equiv of NBS in aqueous THF and a catalytic amount of H2SO4 at 20 degreesC for 5 min gave 2-methylquinoline-5 ,8-dione in 98% yield without bromination. Moreover, we can control either bromination or oxidative demethylation, or both reactions.