Synthesis of Selectively Protected Tri- and Hexaamine Macrocycles

Article abstract of DOI:10.1021/jo00342a006

A general route to tri- and hexaamine macrocycles containing selectively protected diethylenetriamine units has been developed.Condensation of the N'-benzoyl-N,N"-bis(p-tolylsulfonyl)diethylenetriamine N,N"-disodium salt with bissulfonate esters of two-, four-, and six-carbon diols at high reactant concentrations gave the corresponding 9- and 18- (85percent and <1percent), 11- and 22- (30percent and 20percent), and 13- and 26- (56percent and 17percent) membered tri- and hexaamine macrocycles, respectively.The benzoyl group was selectively removed with potassium tert-butoxide in ca. 90percent yield, and the macrocycles were conveniently separated by chromatography.Details of the synthetic procedures and characterization of the new selectively protected tri- and hexaamine macrocycles are described.