Author:
Atkinson Ian M.,Boghai Davar M.,Lindoy Leonard F.,Ghanbari Bahram,Meehan George V.,Saini Vinod
Abstract
The synthesis and characterization of new lipophilic di- and tri-linked
O2N2-donor macrocycles is
reported. The synthesis of the dilinked species involved the initial
alkylation of one secondary nitrogen of the parent 15-membered,
O2N2-donor macrocycle (1) with
2-bromoethanol or with ethylene oxide to yield (2), followed by protection of
the appended alcohol group by reaction with t-butyldiphenylsilyl chloride to
give (3). Two such moieties were then bridged via a diacylation reaction with
ClCO(CH2)8COCl to yield the
corresponding diamide product (4). Deprotection of the alcohol functions
followed by reduction of the both amide linkages resulted in formation of
theN,N′-alkyl-linked species
(5) incorporating two pendant hydroxyethyl groups. This product was then
converted [via the corresponding dichloro derivative (6)] into the
diether (7) by condensation with 4-t-butylphenol.
By use of analogous chemistry, the trilinked trismacrocycle species (12),
based on a phloroglucinol core, has also been synthesized. An aim of the
present study was thus the preparation of new ‘linked’ macrocyclic
systems that might be expected to show higher lipophilicity than their
corresponding single-ring systems. These were designed for future use as
ionophores in metal ion membrane transport (and solvent extraction)
experiments.
Cited by
10 articles.
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