Diaza-crown Ethers. I. Alkali Ion Promoted Formation of Diaza-crown Ethers and Syntheses of Some N,N'-Disubstituted Derivatives.

Abstract

Macrocyclic diazaoligoethers were prepared in relatively good yields from acyclic diiodoethers and diaminoethers at normal concentrations with template ions present. The amines and the iodiodes were prepared from the corresponding dichloroethers, the former via the azides and reduction with hydrogen sulfide and the latter through substitution with iodide ion. 1,7,10,16-Tetraoxa-4,13-diazacyclooctadecane was reacted with ethylene oxide, methoxyethyl p-toluenesulfonate, chloroacetamide and ethyl chloroacetate, respectively, to give disubstituted diaza-crown ethers. The bis (amino acid) was obtained by hydrolysis of the corresponding diester. A toxicity test of some of the diaza-crown ethers shows that the lethal dose is 5-50 mg/kg (mouse, i.v.).