Synthesis and Functionalization of 3-Ethylquinoxalin-2(1H)-one
Synthesis and Functionalization of 3-Ethylquinoxalin-2(1H)-one
复制标题
DOI：
10.1007/s11178-005-0210-2
复制
发表时间：
2005-04
影响因子：
0.8
通讯作者：
V. Mamedov;A. Kalinin;A. Gubaidullin;O. G. Isaikina;I. Litvinov
中科院分区：
文献类型：
--
作者：
V. Mamedov;A. Kalinin;A. Gubaidullin;O. G. Isaikina;I. Litvinov
开发了一种新的有效合成 3-乙基喹喔啉-2(1H)-酮间苯二胺和 2-氧代丁酸乙酯的方法。后者由草酸二乙酯与乙基溴化镁或碘化镁进行格氏反应制备。 3-乙基喹喔啉-2(1H)-one中的乙基可以容易地转化成各种官能团：α-溴乙基、α-硫氰酸基、α-叠氮乙基、α-苯氨基乙基、乙酰基和溴乙酰基。 3-(溴乙酰基)喹喔啉-2(1H)-酮与硫脲和肼-1,2-二硫代甲酰胺反应得到相应的3-(2-氨基-4-噻唑基)衍生物。
A new and effective procedure was developed for the synthesis of 3-ethylquinoxalin-2(1H)-one fromo-phenylenediamine and ethyl 2-oxobutanoate. The latter was prepared by the Grignard reaction of diethyl oxalate with ethylmagnesium bromide or iodide. The ethyl group in 3-ethylquinoxalin-2(1H)-one can readily be converted into various functional groups: α-bromoethyl, α-thiocyanato, α-azidoethyl, α-phenylaminoethyl, acetyl, and bromoacetyl. The reaction of 3-(bromoacetyl)quinoxalin-2(1H)-one with thiourea and hydrazine-1,2-dicarbothioamide gives the corresponding 3-(2-amino-4-thiazolyl) derivatives.