四-(p-羟基苯基)杯[4]间苯二酚芳烃的烃基化和酰胺化反应

Alkylation and Amidation of Tetra(hydroxyphenyl)calix[4]resorcine

间苯二酚和对羟基苯甲醛在盐酸/乙醇中缩合生成四-(p-羟基苯基)杯[4]间苯二酚芳烃(1),在K2CO3/丙酮体系中将1分别与溴乙酸乙酯、溴丙烯、N,N-二丙基氯乙酰胺反应可得到全氧烃基化产物2a～2c.含有12个乙氧基羰基甲氧基支链的2a被苯乙胺、N,N-二甲基二丙胺或三乙烯四胺直接胺解生成杯[4]间苯二酚芳烃酰胺衍生物3a～3c.2a经过碱性水解、酰氯化、胺化反应转化为含吡啶基的酰胺衍生物3d.化合物结构都用1HNMR,IR和元素分析等方法进行了表征.

Tetra（p-hydroxyphenyl）calix[4]resorcine （1）, prepared from the acidic condensation of resorcinol with p-hydroxybenzaldehyde in ethanol, reacted with allyl bromide, ethyl a-chloroacetate or N,N-dipropylchloroacetamide in the system of K2CO3/KI/acetone to yield O-alkylation products 2a-2c. Aminolysis of 12 ethoxycarbonylmethoxy groups in 2a with excess 3-（dimethylamino）propylamine, N-benzyl-N-methylamine or triethylenetetramine to yield amide derivatives 3a-3c in high yields. The pyridine-linked amide derivative 3d was prepared successfully by indirect method from 2a in three steps. The structures of all compounds were characterized with elemental analysis, ^1H NMR and IR spectra.