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

Autor:	Juan Francisco González, Carmen Avendaño, Elena de la Cuesta, Irene Ortín
Rok vydání:	2010
Předmět:	Diketone chemistry.chemical_classification Organic Chemistry Hypervalent molecule Ether Biochemistry Quinone chemistry.chemical_compound chemistry Heterocyclic compound Reagent Drug Discovery Organic chemistry Phenols Demethylation
Zdroj:	Tetrahedron. 66:646-652
ISSN:	0040-4020
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5f848ea002dae0782a33f9ec9056dfaf https://doi.org/10.1016/j.tet.2009.11.070 Zobrazit plný text záznamu Full Text from ScienceDirect