35252-02-9Relevant articles and documents
Oxidative removal of heterocyclic alkyl or sugar side chain by microwave: A simple step to xanthopterin, 6-formylpterin, and 3-hydroxymethyl-2(1H)- quinoxalinone
Goswami, Shyamaprosad,Maity, Annada C.
, p. 1118 - 1119 (2008/02/10)
One-step microwave-assisted oxidative removal of 3-methyl and 3-sugar side chain in 2(lH)-quinoxalinone system by selenium dioxide and sodium periodate respectively resulting 2(1H)quinoxalinone has been reported. Similarly xanthopterin (as acetyl derivative 11) was isolated from selenium dioxide oxidation of 7-methylxanthopterin. In the absence of adjacent lactam moiety, sodium periodate efficiently oxidizes 2-acetylaminopterin tetrols 7 and 8 to 2-acetylamino-6-formylpterin (16) and the quinoxaline tetrols 9 and 10 respectively to quinoxaline aldehyde 17. However, all the compounds remained unchanged on refluxing with selenium dioxide. The new quinoxalone compounds 15 and 18 were simply synthesized by manganese dioxide oxidation of the completely unprotected 3-substituted sugar of 2(lH)-quinoxalinone 5 and quinoxaline 10 respectively under microwave condition. Copyright
Comparative Kinetic Studies on the Synthesis of Quinoxalinone Derivatives and Pyridopyrazinone Derivatives by the Hinsberg Reaction
Bekerman, Diana G.,Abasolo, Maria Ines,Fernandez, Beatriz M.
, p. 129 - 133 (2007/10/02)
Kinetic studies on the anelation of quinoxalinone derivatives 3a-c and pyridopyrazinone derivatives 5a-c and 6a-c synthesized by the Hinsberg reaction is reported. o-Phenylenediamine or 2,3-diaminopyridine were treated with bifunctional carbonyl compounds such as glyoxylic, pyruvic and benzoylformic acids under different experimental conditions.When pyridopyrazine derivatives were synthesized both position isomers were achieved applying regioselective reactions.Mixture were avoided by looking for special experimental conditions that led unambigously to only one of the components of the classic "Hinsberg mixture".Quinoxalinone derivatives 3a-c were obtained at room temperature in good yields (>90percent) using anhydrous methanol or ethanol as solvents.On the other hand, only pyridopyrazin-3(4H)-one (5a) was regioselectively attained in aqueous buffer of pH 7 while 3-methylpyridopyrazinone derivatives were regioselectively separated using anhydrous methanol for one isomer, 5b, and anhydrous chloroform for the other isomer, 6b, at room temperature.Yields were higher than 80percent.Reactions with benzoylformic acid did not give good yields and only 2-phenylpyridopyrazin-3(4H)-one (5c) could be obtained using anhydrous chloroform (yield pyrazin-3(4H)-one (5c) in good yields applying this technique.The other isomer, 3-phenylpyrazin-2(1H)-one (6c) was always formed together with the former isomer and could not be isolated from the mixture, when other solvents than chloroform were used as the reaction media.
3-(1-Piperazinyl)-pyrido[2,3-b]pyrazines
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, (2008/06/13)
3-(1-Piperazinyl)-pyrido[2,3-b]pyrazines and pharmaceutically acceptable salts thereof have serotoninmimetic activity. They are prepared by treating 3-halo-pyrido[2,3-b]pyrazines with piperazine.