Heterocyclic analogs of 5,12-naphthacenequinone 10.* Synthesis of furanoquinizarine and its new derivatives

Autor:	Andrey E. Shchekotikhin, Yu. N. Luzikov, Maria N. Preobrazhenskaya, Alexander S. Tikhomirov, Alexander M. Korolev
Rok vydání:	2012
Předmět:	chemistry.chemical_compound Hydrolysis chemistry Bromoacetic acid Salicylaldehyde Decarboxylation Furan Organic Chemistry Organic chemistry Alkylation Anthraquinone Demethylation
Zdroj:	Chemistry of Heterocyclic Compounds. 47:1206-1211
ISSN:	1573-8353 0009-3122
Popis:	A new method was developed for synthesis of anthra[2,3-b]furan-5,10-dione derivatives. The key compound for annelation of the furan fragment to the anthraquinone chromophor is the previously unknown analog of salicylaldehyde, 1,4-dimethoxy-3-formyl-2-hydroxyanthraquinone, which we have synthesized by the Miller–Loudon–Schneider reaction. A chain of sequential transformations was used for its conversion into the target 4,11-dihydroxyanthra[2,3-b]furan-5,10-dione (furanoquinizarine): O-alkylation of the starting formylhydroxyanthraquinone with bromoacetic acid esters, cyclo-dehydration of the 3-formylanthraquinon-2-ylacetic acid esters in the presence of bases, hydrolysis of the obtained esters to 4,11-dimethoxy-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-2-carboxylic acid, its decarboxylation, and demethylation of the obtained 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6b2e3840951225062bdbd7a4b144efa3 https://doi.org/10.1007/s10593-012-0895-4 Zobrazit plný text záznamu Plný text ve formátu PDF