乙酰乙酰苯胺类化合物导向的2,2-二溴乙酰苯胺衍生物的合成有机化学.pdfVIP

    DOI: 10.6023/cjoc201410008  研究简报 有机化学 Chinese Journal of Organic Chemistry  NOTE  乙酰乙酰苯胺类化合物导向的2,2-二溴乙酰苯胺衍生物的合成 刘卫兵* 陈 翠 邱会华 (广东石油化工学院 化学工程学院 茂名 525000) 摘要 以 N-溴代丁二酰亚胺(NBS)为溴源, 醋酸为催化剂和溶剂, 经过活泼亚甲基的两次连续的溴化, 羰基的质子化 和碳碳键的断裂等过程合成了 2,2-二溴乙酰苯胺衍生物. 该方法具有操作简便、反应条件温和和高效等特点. 所有反 应都能以极高的收率得到相应的目标产物. 关键词 碳溴键形成; 碳碳键断裂; 2,2-二溴乙酰苯胺衍生物; 乙酰乙酰苯胺类化合物 An Efficient Access to α-Dibromosubstituted Arylamides from β-Keto Arylamides Liu, Weibing* Chen, Cui Qiu, Huihua (College of Chemcal Engineering, Guangdong University of Petrochemical Technology, Maoming 525000) Abstract A remarkably simple, mild and efficient approach for carbon-carbon bond cleavage of β-keto amides using N-bromobutanimide (NBS) as the bromine source and acetic acid as the catalyst to construct α-dibromosubstituted arylamides is achieved. Moreover, tandem carbon-bromine bond formation, followed by protonation of carbonyl and cleavage of C—C bond in one pot has also been demonstrated. All the reactions were carried out under extremely mild conditions and provided almost quantitative yields of the products. Keywords carbon-bromine bond formation; carbon-carbon bond cleavage; α-dibromosubstituted arylamides; acetoacetani- lides 由于乙酰乙酰苯胺类化合物分子具有多个反应活 机合成中, 并且有大量的文献对其进行了报道[21,22]. 然 性位点[1,2], 所以该类化合物在有机合成中是一类倍受 而, 以NBS 为溴源, 对同一个碳经历两次连续溴化过程 关注和倍受欢迎的有机原料[3～6],