Reactions promoted by [hydroxy(tosyloxy)iodo]benzene in pyrazino[1,2–b]isoquinolines

The hypervalent iodine reagent PhI(OH)OTs (HTIB) promoted oxidative demethylation of 1,4-hydroquinone methyl ethers to give quinones in a quantitative conversion. The efficacy of this reaction, that has been applied to simple arene compounds and to heterocyclic systems, such as 2-isopropoxycarbonyl-...

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Bibliographic Details
Published in:Tetrahedron 2010-01, Vol.66 (3), p.646-652
Main Authors: Ortín, Irene, González, Juan Francisco, Cuesta, Elena de la, Avendaño, Carmen
Format: Article
Language:English
Subjects:
Antitumor agents
Chemistry
Exact sciences and technology
Heterocycles
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hypervalent iodine
Noncondensed benzenic compounds
Organic chemistry
Oxidations
Preparations and properties
Quinones
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Summary:The hypervalent iodine reagent PhI(OH)OTs (HTIB) promoted oxidative demethylation of 1,4-hydroquinone methyl ethers to give quinones in a quantitative conversion. The efficacy of this reaction, that has been applied to simple arene compounds and to heterocyclic systems, such as 2-isopropoxycarbonyl-7,10-dimethoxy-pyrazino[1,2–b]isoquinoline-4-ones and 1,4-diones to get the corresponding 7,10-quinones (compounds 6–8), is similar to those promoted by CAN and does not require the presence of water. Instead of oxidative demethylation, HTIB promoted in 1-methoxy-pyrazino[1,2–b]isoquinoline-4-ones complex multi-step processes to give compounds 9 or 10. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.11.070