An expedient synthesis of N-tosyl macrocycles containing two thiourea moieties from trisulfonamide and bis-dithiocarbamate salts at room temperature in aqueous media

Abstract

The nucleophilic reaction of diamines and carbon disulfide in aqueous NaOH afforded a series of bis-dithiocarbamate salts. Activation of these with aqueous ClCH2COOK and subsequent nucleophilic substitution reaction with trisulfonamide aqueous KOH at room temperature provided N-tosyl-macrocycles containing two thiourea units. This strategy has the advantages of simple operation, mild reaction condition, easy product-isolation and environmental friendliness. © ARKAT USA, Inc.