硫酸氢钾催化一锅法合成1-乙酰胺烷基-2-萘酚.pdf

第23卷第1期
化学研究
中国科技核心期刊
2012年1月
CHEMICAL RESEARCH
hxy@henu.edu.cn
硫酸氢钾催化一锅法合成1-乙酰胺烷基-2-萘酚
何建英,史利勇,杨一可,陈丹云
(河南大学化学化工学院,河南开封475004)
摘要:以硫酸氢钾为催化剂,在无溶剂条件下催化-禁酚和乙酰胺分别与苯甲醛、对硝基苯甲醛、水杨醛、茴香
醛、香兰素等五种芳香醛的三组分反应,利用一锅法合成了系列1-乙酰胺烷基-2-萘酚.以1-乙酰胺基苯甲基-2
茶酚(AAN)的合成为模板反应考察了催化剂用量、反应温度、原料配比及反应时间等因素对产物收率的影响
结果表明,硫酸氢钾催化合成AAN反应的适宜条件为:n(2-萘酚):n(苯甲醛):n(乙酰胺):n(硫酸氢钾)
1:1.2:1.2:0.05,90℃下反应40min,AAN的收率达92.1%、硫酸氢钾对其他四种反应地有较理想的催化
作用,目标产物收率为69.1%~94.0%
关键词:硫酸氢钾;一锅法;1-乙酰胺烷基-2-禁酚;1-乙酰胺基苯甲基-2-装酚;催化合成
中图分类号:O621.3
文献标志码:A
文章编号:1008-1011(2012)01-0085-04
One-pot synthesis of 1-acetamidoalkyl-2-naphthols
catalyzed by potassium bisulfate
HE Jian-ying, SHI Li-yong, YANG Yi-ke, CHEN Dan-yun
(College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, Henan, China
Abstract: Potassium bisulfate was used as catalyst to catalyze the three-component reactions
among 2-naphthol plus acetamide and five kinds of arylaldehydes including benzaldehyde, t-ni-
tro benzaldehyde
licylic aldehyd
aldehyde, and vanillic aldehyd
elding a
1-acetamidoalky1-2-naphthols
the absence of
effects of catalyst dosage, temperature, molar ratio of starting materials, and reaction time on
the yield were investigated using the reaction for synthesizing N-lphenyl-(2-hydroxy-naptha-
lene-1-y1)-mehtyl]-acetamide(AAN) as a template reaction. As the results, the optimal con
dition for synthesizing AAN is suggested as reaction temperature 90 C, molar ratio of starting
materials n(2-naphthol): n(benzaldehyde): n(acetamide): n(potassium bisulfate) =1: 1
1.2: 0.05, and reaction time40 min, with the yield being 92. 1%. Besides, potassium bisu-
ate also has good catalytic performance for the reactions of 2-naphthol plus acetamide with the
other four kinds of arylaldehydes, with the yields of 69.1%-94.0%
Keywords: potassium bisulfate; one-pot method 1-acetamidoalkyl-2-naphthols; N-lphenyl-(2
hydroxy-napthalene-1-y1)-mehty1]-acetamide; catalytic synthesis
1-乙酰胺基烷基2茶酚可通过酰胺基水解转化为具有生物活性的1-氨基烷基-2-萘酚行生物,后者具有
治疗低血压和心动过缓等功效.2006年 KHODAEIM首次报道用对甲苯磺酸催化酰胺或脲与芳香醛和
收稿日期:2011-08-16.
基金项目:河南省科技斤2011年科技发展计划项日(112102210008)
作者简介:何建英(1959-),女,高级实验师,主要从事精细化学品的催化合成研究.“通讯联系人