Synthesis of macroheterocyclic analogs of dibenzocrown-compounds. 3. 18-Membered oxathiazacrown-compounds

Abstract

Condensation of 1,7-bis(2-aminophenyl)-4-thia-1,7-dioxaheptane with dichloroanhydrides of glutaric, diglycolic, thiodiglycolic, and N-tosyliminodiacetic acids under high dilution conditions with subsequent reduction of the macrocyclic diamides by borohydride leads to formation of 18-membered macrocylic diamines which contain a sulfur atom in the 4 position. An analogous series of reactions using 1,7-bis(2-aminophenyl)-4-(carba, oxa, aza)-1,7-dioxaheptanes and the dichloroanhydride of thiodiglycolic acid allows the sulfur atom to be introduced in the 13 position. The structure of the synthesized compounds was confirmed by IR, NMR, and mass spectral data.