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The synthesis of macrocyclic polyether‐diester compounds with a pyridine subcyclic unit
Author(s) -
Bradshaw J. S.,
Asay R. E.,
Maas G. E.,
Izatt R. M.,
Christensen J. J.
Publication year - 1978
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.5570150522
Subject(s) - chemistry , pyridine , potassium thiocyanate , chloride , thiocyanate , medicinal chemistry , potassium , ethylene , organic chemistry , catalysis
Abstract Two new series of macrocyclic polyether‐diester ligands ( 4‐15 ) containing a pyridine subcyclic unit have been prepared by treating various oligoethylene glycols and sulfur‐containing oligo‐ethylene glycols with 2,6‐ and 3,5‐pyridine dicarbonyl chlorides. The compounds prepared from 2,6‐pyridine dicarbonyl chloride were: 3,6,9,12‐tetraoxa‐18‐azabicyclo[12.3.1 ]oetadeca‐1(18), 14,16‐triene‐2,13‐dione ( 4 ); 3,6,9,12,15‐pentaoxa‐21‐azabieyclo[15.3.1]heneicosa‐1(21),17,19‐triene‐2,16‐dione ( 5 ); 3,6,12,15‐tetraoxa‐9‐thia‐21‐azabicyclo[15.3.1 ]heneicosa‐1(21),17,19‐tri‐ene‐2,16‐dione( 6 ); 3,9,15‐trioxa‐6,12‐dithia‐21‐azabicyclo[15.3.1]heneicosa‐1(21),17,19‐triene‐2,16‐dione ( 7 ); 3,6,9,12,15,18‐hexaoxa‐24‐azabicyclo[18.3.1 ]tetracosa‐1(24),20,22‐triene‐2,19‐dione ( 8 ); 3,6,9,12,15,18,21‐heptaoxa‐27‐azabicyclo[21.3.1]heptacosa‐1(27),23,25‐triene‐2,22‐dione ( 9 ); and the corresponding analogues from 3,5‐pyridine dicarbonyl chloride ( 10‐15 ). The solid potassium thiocyanate complex of compound 5 was also prepared.