Capping methodology in cyclodextrin chemistry: use of a symmetrical diketone reagent for regiospecific installation of unsymmetrical imine-enamine and imidazole caps.
Chemistry
; 20(9): 2565-73, 2014 Feb 24.
Article
em En
| MEDLINE
| ID: mdl-24488585
ABSTRACT
Methylated α- and ß-cyclodextrin skeletons were both equipped with an unsymmetrical N-(2-N-alkylaminoacenaphthenyl)alkylimine rigid handle. The capping reaction, which consists of condensing a diaminocyclodextrin with highly symmetrical acenaphthenequinone, was found to be regiospecific when starting from cyclodextrin-diamines without any symmetry element. All modified cyclooligosaccharides have intra-annular nitrogen donor atoms. They undergo further cyclization on oxidation, whether chemically with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or electrochemically, to give highly strained cyclodextrins capped with an unsymmetrical 1,2-disubstituted 1H-imidazole unit.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
Chemistry
Assunto da revista:
QUIMICA
Ano de publicação:
2014
Tipo de documento:
Article