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Regioselective synthesis and characterization of naphthylethylcarbamoyl-β-cyclodextrins

✍ Scribed by K.H. Gahm; W. Yoshida; W.P. Niemczura; A.M. Stalcup

Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
691 KB
Volume
248
Category
Article
ISSN
0008-6215

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✦ Synopsis

Regioselective reactions of 1-(1-naphthyl)ethyl isocyanate (NEIC) with beta-cyclodextrin (beta-CD) were studied with and without NaH activation of beta-CD in N,N-dimethylformamide (DMF) and pyridine. All six possible monosubstituted CD products were separated and characterized by proton NMR. Primary substitution product predominates when the reaction was carried out under reflux condition in pyridine without NaH activation. The C-2 substitution product predominates when the reaction was carried out in DMF. Conversion of 2-O-(1-(1-naphthyl)ethylcarbamoyl)-beta-CD to 6-O-(1-(1-naphthyl)ethylcarbamoyl)-beta-CD was observed when NaH was used to activate hydroxyl groups of CD.

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