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系列新型硫杂杯[4]芳烃氮杂衍生物的合成
引用本文:杨发福,赵夏,杨娥,郭红玉,黄翠玉.系列新型硫杂杯[4]芳烃氮杂衍生物的合成[J].有机化学,2007,27(5):670-673.
作者姓名:杨发福  赵夏  杨娥  郭红玉  黄翠玉
作者单位:福建师范大学化学与材料学院,福州,350007
基金项目:国家自然科学基金(No.20402002)和福建省自然科学基金(Nos.E0220002,2006J0155)资助项目
摘    要:在对叔丁基硫杂杯4]芳烃的下缘1,3位引入芳醛基, 合成了硫杂杯4]二醛基衍生物2. 化合物2与苯胺、水杨酰肼、烟酰肼、异烟酰肼等通过席夫碱缩合反应得到新型硫杂杯4]氮杂衍生物3a3d, 产率分别为83%, 80%, 77%和79%. 化合物2与邻苯二胺、乙二酰肼、丙二酰肼、己二酰肼等通过“1+1”分子间缩合得到新型1,3-桥联硫杂杯4]氮杂衍生物4a4d, 产率53%, 51%, 59%和66%. 新化合物的结构经IR, 1H NMR, MS和元素分析等证实.

关 键 词:硫杂杯[4]芳烃  酰肼  席夫碱  合成
收稿时间:2006-9-21
修稿时间:2006-09-21

Syntheses of Novel Thiacalix[4]arene Aza Derivatives
YANG Fa-Fu,ZHAO Xi,YANG E,GUO Hong-Yu,HUANG Cui-Yu.Syntheses of Novel Thiacalix[4]arene Aza Derivatives[J].Chinese Journal of Organic Chemistry,2007,27(5):670-673.
Authors:YANG Fa-Fu  ZHAO Xi  YANG E  GUO Hong-Yu  HUANG Cui-Yu
Institution:College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007
Abstract:Thiacalix4]arene bi-benzaldehyde derivative 2 was synthesized by introducing benzaldehyde groups on 1,3-position of p-tert-butylthiacalix4]arene. Reacting compound 2 with aniline, salicylic hydrazide, nicotinic hydrazide or isonicotinic hydrazide gave series of novel thiacalix4]arene aza derivatives 3a3d by the Schiff-base condensation in the yields of 83%, 80%, 77% and 79%, respectively. Treatment compound 2 with o-phenylendiamine, oxalyl dihydrazide, malonic dihydrazide and adipic dihydrazide afforded novel bridged thiacalix4]arene aza derivatives 4a4d by “1+1” condensation in the yields of 53%, 51%, 59% and 66%. The structures of all new compounds were characterized by IR, ESI-MS, 1H NMR spectra and elemental analyses.
Keywords:thiacalix[4]arene  hydrazide  Schiff-base  synthesis
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