Improved Arndt-Eistert Synthesis of α-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger
Improved Arndt-Eistert Synthesis of α-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger
复制标题
DOI：
10.1021/jo101105g
复制
发表时间：
2010-08-20
影响因子：
3.6
通讯作者：
De Kimpe, Norbert
中科院分区：
文献类型：
--
作者：
Pace, Vittorio;Verniest, Guido;De Kimpe, Norbert
介绍了一种通过改进的Arndt-Eistert合成获得α-重氮酮的实用方法。该方法允许在氧化钙存在下使用化学计量的重氮甲烷有效地转化酸性卤化物，而不会伴随乙酮或卤代酮的生成。得到的α‘-溴代-α-重氮酮可作为合成感兴趣的α-芳氨基-α’-卤甲基酮的合适底物。
A practical methodology to obtain alpha-diazoketones through an improved Arndt-Eistert synthesis is described. The method allows the efficient transformation of acid halides using a stoichiometric amount of diazomethane in the presence of calcium oxide, without concomitant ketene or haloketone formation. The obtained alpha'-brominated-alpha-diazoketones were employed as suitable substrates for the synthesis of interesting alpha-arylamino-alpha'-halomethylketones.