SYNTHESIS AND COMPLEXATION PROPERTIES OF PYRIMIDINE-DERIVED CROWN-ETHER LIGANDS[1]

Citation
Jt. Redd et al., SYNTHESIS AND COMPLEXATION PROPERTIES OF PYRIMIDINE-DERIVED CROWN-ETHER LIGANDS[1], Journal of heterocyclic chemistry, 35(1), 1998, pp. 1-8
Citations number
42
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0022-152X
Volume
35
Issue
1
Year of publication
1998
Pages
1 - 8
Database
ISI
SICI code
0022-152X(1998)35:1<1:SACPOP>2.0.ZU;2-M
Abstract
Five new proton-ionizable macrocyclic ligands containing a pyrimidone- subcyclic unit, 6-10, were prepared from the previously prepared pyrim idinocrown ethers 1-5 (see Figure 1 and Scheme 1). One of the new prot on-ionizable crown ethers is chiral. The proton-ionizable pyrimidonocr own ethers were prepared in high yields by treating the appropriate me thoxy-substituted pyrimidinocrown with 5 M sodium hydroxide in a 50% a lcohol-water mixture. Complexation properties of four of the pyrimidin e-derived macrocycles were studied by various nmr techniques. Pyrimido no-18-crown-6 (9) forms a strong complex with benzylammonium perchlora te and also forms a complex with benzylamine. (S,S)-Dimethyl-substitut ed pyrimidino- and pyrimidono-18-crown-6 ligands 4 and 9 form stronger complexes with the (R)-form of alpha-(1-naphthyl)ethylammonium perchl orate than with the (S)-form. (S,S)-Dimethyl-substituted pyrimidono-18 -crown-6 (9) also forms a stronger complex with (R)-alpha-(1-naphthyl) ethylamine than with the (S)-form. The crystal structure for compound 7 is reported.