112010-10-3Relevant academic research and scientific papers
Meerwein Arylation of Methyleneglutaronitrile with Anthraquinone Diazonium Hydrogensulfate. Synthesis of an Enolizable Benzanthrone Lactone
Sutter, P.,Weis C.D.
, p. 69 - 74 (2007/10/02)
The Meerwein reaction of 1-anthraquinone diazonium hydrogensulfate with 2-methyleneglutaronitrile in methanol yielded predominantly 3-hydroxy-4-(1-anthraquinone)-1,3-butanedicarbonitrile (5), while the corresponding 2-methyleneglutaric acid diethyl ester furnished a derivative of 1-(anthraquinone)butanolide 10.Catalytic dehydrocyanation of 5 was effected with Dowex-50 to furnish 3-oxo-4-(anthraquinone)butanecarbonitrile (6).Both nitriles 5,6 gave in a double cyclization reaction a benzanthrone lactone 12 from which a crystalline derivative of the enol form was isolated, the structure of which was elucidated by 1H- and 13C-nmr spectra.The methylene group of the lactone ring underwent coupling reactions with aromatic diazonium salts to form hydrazone derivatives.
