REGIOSELECTIVE SYNTHESIS AND CHARACTERIZATION OF NAPHTHYLETHYLCARBAMOYL-BETA-CYCLODEXTRINS

Regioselective reactions of 1-(1-naphthyl)ethyl isocyanate (NEIC) with beta-cyclodextrin (beta-CD) were studied with and without NaH activat ion of beta-CD in N,N-dimethylformamide (DMF) and pyridine. All six po ssible monosubstituted CD products were separated and characterized by proton NMR. Primary substitution product predominates when the reacti on was carried out under reflux condition in pyridine without NaH acti vation. The C-2 substitution product predominates when the reaction wa s 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 wh en NaH was used to activate hydroxyl groups of CD.