Tetrahedron Letters p. 1027 - 1029 (2002)
Update date:2022-07-31
Topics:
Hortala, Laurent
Moberg, Christina
Levacher, Vincent
Bourguignon, Jean
Dupas, Georges
A significant acceleration of acyl transfer has been achieved on 8-acetoxy-2-oxazolinylquinoline in the presence of benzylamine. Comparison of the aminolysis by the new acylating reagent with that of 8-acetoxyquinoline and 8-acetoxyquinoline-2-carbonitrile has been carried out. The results of these experiments suggest that the proximity of a supplementary basic atom to the ester group increases the participation effect of the basic site mainly by formation of a possible second hydrogen bond. The association constant of benzylamine into the basic cavity of 8-methoxy-2-oxazolinylquinoline (Ka=80 M-1) has been measured by 1H NMR titration experiments.
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