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Proton‐ionizable crown compounds. 9 . Synthesis and structural studies of new 14‐crown‐4 compounds containing a pyridine or 4‐pyridone subcyclic unit
Author(s) -
Bradshaw Jerald S.,
Guynn John M.,
Wood Steven G.,
Wilson Bruce E.,
Kent Dalley N.,
Izatt Reed M.
Publication year - 1987
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.5570240222
Subject(s) - chemistry , 2 pyridone , pyridine , propane , diol , hydrocarbon , 18 crown 6 , crown (dentistry) , medicinal chemistry , organic chemistry , molecule , medicine , dentistry
Four new 14‐crown‐4 macrocyclic ligands containing either a pyridine or a 4‐pyridone subcyclic unit have been prepared. Two of the 4‐pyridono‐crowns contained lipophilic hydrocarbon substituents. The starting octyl‐ and benzyl‐substituted 4‐oxa‐1,7‐heptanediols were prepared from the 2‐octyl‐ or 2‐benzyl‐1,3‐propane‐diol. When the two substituted 4‐oxa‐1,7‐heptanediols were treated with tosyl chloride, both the expected 2‐substituted‐4‐oxaheptane‐1,7‐ditosylates and the ditosylate of the dimeric diol were isolated. X‐ray structure determinations were carried out on two of the new 14‐crown‐4 compounds.