摘要
以碳酸钾为缩合剂２，２’－二羟基联苯分别与二对甲苯磺酸酯Ⅱａ～ｃ，Ⅳｂ，Ⅵｂ反应合成尚未见文献报道的联苯型单氮杂冠醚（１～３），二氮杂冠醚９和１１，３，９和１１分别用氢溴酸去甲苯磺酰基得到亚胺型氮杂冠醚４，１０和１２。４与溴代烃ＲＢｒ（ｒ＝－（ＣＨ２）３ＣＨ３－ＣＨ２ＣＨ＝ＣＨ２－（ＣＨ２）７ＣＨ３－（ＣＨ２）２Ｏ（ＣＨ２）２ＯＣ４Ｈ９）反应分别合成（１１）环系氮支套索冠醚（５～８）。
New diphenyl 11 - membered ring aza crown ethers(l - 3), 14 and 17 - membered ring diazacrown ethers(9, 11) were prepared by ome step reaction of 2, 2' - dihydroxydephenyl with com-pouds TsO(CH2CH2N)m(CH2CH2O)nCH2CH2NCH2CH2OT3( Ⅱ a: m = n = 0, R = C6H5 - ; Ⅱ b: m =n=0,R=p-CH3C6H4;22222c:m = n = 0, R = Ts;Ⅳ b: m = 1, n = 0, R = Ts;Ⅵ b: m = n =1,R=Ts; Ts= tosy1) in DMF at 100 - 110℃ , using anhydrous patassium carbonate as condensing agent. The tosyl groups of 3, 9 and 11 were removed by treatment with 40 % HBr in ACOH in the presence of a large amount of phenol. Three new azacrown ethers 4, 10 and 12 were formed from 3, 9 and 11 respectively. New N - pivot lariat crown ethers 5 -8 and 13 were prepared by one step reaction of 4 and 12 with RBr in CH3Cn at reflux temperature, using anhydrous K2CO3 as condensing ageny. They were characterized by elemental analysis, IR, 1H NMR and MS.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
1996年第1期23-28,共6页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金
关键词
二羟基联苯
氮朵冠醚
合成
2,2'- dihydroxydiphenyl, N - pivot lariat crown ether, synthesis
