Improved synthesis of symmetrically & asymmetrically N-substituted pyridinophane derivatives.

ABSTRACT: The N,N'-di(toluenesulfonyl)-2,11-diaza[3,3](2,6)pyridinophane (^TsN4) precursor was sought after as a starting point for the preparation of various symmetric and asymmetric pyridinophane-derived ligands. Various procedures to synthesize ^TsN4 had been published, but the crucial problem had been the purification of ^TsN4 from the larger 18- and 24-membered azamacrocycles. Most commonly, column chromatography or other laborious methods have been utilized for this separation, yet we have found an alternate selective dissolution method upon protonation which allows for multi-gram scale output of ^TsN4·HCl. This optimized synthesis of ^TsN4 also led to the development of symmetric ^RN4 derivatives as well as the asymmetric derivative

SUBMITTER: Wessel AJ 

PROVIDER: S-EPMC7716245 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature