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The synthesis of novel macrocyclic multidentate compounds from dioxodioic acids
Author(s) -
Asay R. E.,
Bradshaw J. S.,
Nielsen S. F.,
Thompson M. D.,
Snow J. W.,
Masihdas D. R. K.,
Izatt R. M.,
Christensen J. J.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140116
Subject(s) - chemistry , denticity , maleic acid , organic chemistry , ethylene diamine , polymer chemistry , copolymer , crystal structure , nuclear chemistry , polymer
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).