新型醚键连接的杂环功能基杯[4]芳烃衍生物的合成及结构

Synthesis and Structures of p-tert-Butylcalix[4]arene Derivatives Containing Heterocycle Functional Groups Tethered by Ether Bridges

以碘化钠为催化剂,在氢氧化钠存在下2-氯乙氧基乙醇分别与2-巯基芳香杂环化合物反应制得相应的芳香杂环衍生物1a～1e.以三乙胺为缚酸剂,其与对甲苯磺酰氯反应,生成了活化羟基的衍生物2a～2e.在碳酸钾存在下,对叔丁基杯[4]芳烃分别与2a～2e反应生成醚键连接的杂环功能基杯[4]芳烃衍生物3a～3e,并通过1HNMR,13CNMR,IR,MS和元素分析的确证.同时,X射线分析确定了杯[4]芳烃3a,3b和3d的晶体结构.

Five 2-（2-heterocycle-2-ylthioethoxy）ethanols 1a ～ 1e were prepared by the reaction of 2-（2-chloroethoxy）ethanol and 2-mercapto-heterocycles using sodium iodide as catalyst.Consequently,the compounds 1a～1e reacted with tosyl chloride to afford corresponding tosylates 2a～2e.A series of p-tert-butylcalix[4]arene derivatives 3a～3e which contain heterocycle functional groups tethered by ether bridges were easily synthesized by the reaction of p-tert-butylcalix[4]arene with tosylated 2a～2e in the presence of potassium carbonate,respectively.All new compounds were characterized by ^1H NMR,^13C NMR,IR,MS techniques and elemental analysis.Meanwhile,the structures of calix[4]arene derivatives 3a,3b and 3d were identified by X-ray diffraction analysis.