The synthesis and binding characters of 1,3-bis(uracil-1/3-ylmethyl)benzene based acyclic and cyclic receptors

Abstract

The phase transfer catalysed reactions of 1,3-bis(uracil-1-ylmethyl)-2-methoxy-5-methylbenzene <b>2</b> with 2-bromoethyl methyl ether, 2-bromoethyl 2-butoxyethyl ether, 1,5-dibromo-3-oxapentane, 1,8-dibromo-3,6-dioxaoctane and 1, 11-dibromo-3,6,9-trioxaun-decane provide respective acyclic receptors <b>4a,b</b> and cyclic receptors <b>6a-c</b>. 1,14-Bis(uracil-1-yl)-3,6,9, 12-tetraoxa-2, 13-dioxotridecane <b>16</b> reacts with 1,3-bis(bromomethyl)-2-methoxy/ acetoxy-5-methylbenzene to give cyclic receptors <b>17a, b</b>. The studies on the representative cases reveal that <b>17b</b>, wherein 1,3-arylidene unit is placed between N-3 positions of two uracils shows much higher order of ionophore character than <b>4a, 4b</b> and <b>6b</b>, wherein 1,3-arylidene unit is present between N-1 positions of uracils.