THE SYNTHESIS OF NEW DIAZA-N-PIVOT LARIAT 15-CROWN-5 AND 18-CROWN-6 MACROCYCLES

Nine diaza-15-crown-5 and nine diaza-18-crown-6 macrocycles containing tertiary aminoalkyl and hydroxyalkyl side groups attached to one of the ring nitrogen atoms have been prepared in good yields. The ring closure step involved the reaction of a bis-secondary amine containing the tertiary aminoalkyl or hydroxyalkyl substituent with ethylene glycol bis-(2-iodoethyl)ether or diethylene glycol bis-(2-chloroethyl)ether plus sodium iodide. The starting tertiary aminoalkyl- or hydroxyalkyl-substituted bis-secondary aimine was prepared by reacting N-[2-(2-chloroethoxy)ethyl]acetamide or its benzamide analogue with a primary amine. © 1990.