Synthesis of pentadentate mixed N/S dithiolate chelating ligands derived from heterocycles and 2-mercaptoethylamines

Article abstract of DOI:10.1016/S0040-4039(99)00757-1

Condensation of 2,6-pyridinedialdehyde with 2-mercaptoethylamines or 2- alkylthioethylamines yielded 2,6-bis(substituted-2-thiazolidinyl)pyridine or 2,6-bis-((2-alkyl-thio)ethylimino)methylpyridine. The thiazolidines can be reductively opened to give 2,6-bis-((substituted-2- thioethyl)aminomethyl)pyridines. Alternatively, the latter may be synthesized by reductive amination of 2,6-pyridinedialdehyde with 2-mercaptoethylamines. Reaction of 2,5-thiophenedicarbonyl chloride with 2-mercaptoethylamines led to N,N'-bis(substituted-2-thioethyl)2,5-thiophenedicarboxamides. 2,6-Bis- ((substituted-2-thioethyl)aminomethyl)pyridines and N,N'-bis(substituted-2- thioethyl)-2,5-thiophenedicarboxamides are novel pentadentate mixed N/S dithiolate chelating reagents which can form ferric complexes of biomimetic importance.