The synthesis of novel macrocyclic multidentate compounds from dioxodioic acids

Abstract

Abstract A series of novel macrocyclic multidentate crown compounds have been prepared from a series of dioxodioic acids. The dioxodioic acids were prepared by treating various oligoethylene glycols or amines with maleic, succinic, citraconic, and glutaric anhydrides. The crown compounds were then synthesized from the dioxodioic acid chlorides obtained from the diacids and various oligoethylene glycols or ethylene diamine. The following macrocyclic compounds have been prepared: 1,4,9,12‐tetraoxacyclohexadecane‐5,8,13,16‐tetrone ( 1 ); 1,4,7,10,15,18‐hexaoxacyclodocosane‐11,14,19,22‐tetrone ( 2 ); 1,4‐dioxa‐9,12‐diazacyclohexadecane‐5,8,13,16‐tetrone ( 3 ); 1,4,7‐trioxa‐12,15‐diazacyclonoadecane‐8,11,16,19‐tetrone ( 4 ); 1,4,7,10‐tetraoxa‐15,18‐diazacyclodocosane‐11,14,19,22‐tetrone ( 5 ); 4‐benzyl‐1,7,12,15‐tetraoxa‐4‐azacyclonona‐decane‐8,11,16,19‐tetrone ( 6 ); 1,4,7,12,15,18‐hexaoxacyclodocosa‐9,20‐diene‐8,11,19,22‐tetrone( 7 ); and 9,21‐dimethyl‐1,4,7,12,15,18‐hexaoxacyclodocosa‐9,20‐diene‐8,11,19,22‐tetrone ( 8 ) (Figure 1).