Development of N,N-BIs (2-hydroxyalkylbenzyl) alkylamine derivatives to crown ethers based macrocycles

Abstract

The present work focuses on the development of N,N-bis(2-hydroxyalkyl benzyl)alkylamine derivatives to crown ether based macrocycles. As N,N-bis(2-hydroxyalkyl benzyl) alkylamine derivatives consist of two phenol units linked with aza-methylene linkage under the strong networks of inter- and intramolecular hydrogen bonds, their unique structures are expect for providing a specific macrocyclization. The first part involves with [1+1] and [2+2] crown ethers derived from N,N-bis(2-hydroxyalkyl benzyl) alkylamine with or without ortho-substituted group in phenol group. The first part also covers the inclusion phenomena of the selective macrocycles with alkali ions. The second part is about a variety of macrocycles after cyclization with various chain lengths of ditosylated compound induced by the structure of N,N-bis(2-hydroxyalkyl benzyl) alkylamine itself. In the third part, synergistic effects of a specific metal template and H-bonds in controlling macrocyclization of N,N-bis(2-hydroxyalkyl benzyl) alkylamine derivatives to obtain a single type of macrocycle are reported. The final part concentrates on a simple but effective preparation of ring-enlarged dibenzo-monoaza-crowns and how their structures are involved with the metal ion selectivity.