铜纳米颗粒催化合成3-取代异香豆素及其衍生物
Synthesis of 3-substituted isocoumarins and its derivatives by copper nanoparticles catalyst
作者:范兴风;王德才;王鑫;高瑞;
Author:
收稿日期: 年卷(期)页码:2017,32(06):-573-575
期刊名称:华西药学杂志
Journal Name:WEST CHINA JOURNAL OF PHARMACEUTICAL SCIENCES
关键字:铜纳米颗粒;3-取代异香豆素;衍生物;催化;合成
Key words:
基金项目:
中文摘要
目的制备3-取代异香豆素及其衍生物。方法以邻卤代苯甲酸为起始原料,通过卤化、酰胺化,得N-苯基-2-卤代苯甲酰胺衍生物,在铜纳米颗粒催化下与1,3-二羰基化合物反应,得到目标化合物。结果合成了3-取代异香豆素,其结构经1HNMR和ESI-MS确证。结论所用方法反应的原料简单易得、产物收率较高,可高效合成3-取代异香豆素,拓展了3-取代异香豆素的合成方法。
参考文献
[1]Takeo YS,Ryoich MJ,Hirosh T,et al.Antibiotic M143-37F11and its manufacture and synthetic intermediates[P].JP Patent:JP 04112884.1992-04-14.
[2]Ryoich M,Takeo Y.Preparation of anticancer isocoumarins[P].JP Patent:JP 0597841.1993-04-20.
[3]Harper JW,Hemmi K,Powers JC.Reaction of serine proteases with substituted isocoumarins:Iscovery of 3,4-dichloroisocoumarin,a new general mechanism based serine protease inhibitor[J].Biochemistry,1985,24(8):1831-1841.
[4]Sakamoto T,Naka MA,Kondo Y,et al.Condensed heteroaromatic ring systems VIII.Synthesis of 3-substitued isocoumarins from o-halobenzoic acid derivatives[J].Chem Pharm Bull,1986,34(7):2754-2759.
[5]Kurune A,Kanata Y,Yamashita M,et al.Synthesis of 3-substituted isocoumarins and their inhibitory effects on degranulation of RBL-2H3 cells induced by antigen[J].Chem Pharm Bull,2008,56(9):1264-1269.
[6]Peuchmaur M,Lisowski V,Gandreuil C,et al.Solid-phase synthesis of isocoumarins:A traceless halocyclization approach[J].J Org Chem,2009,74:4158-4165.
[7]Tajudeen SS,Khan FN.Synthesis of some 3-substituted isochromen-1-ones[J].Synthetic Communications,2007,37:3649-3656.
【关闭】