Acyl transfer of 8-acetoxy-2-oxazolinylquinoline assisted by hydrogen bonding formation
2002 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1873-3581, Vol. 43, no 6, 1027-1029 p.Article in journal (Refereed) Published
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 (K-d = 80 M-1) has been measured by H-1 NMR titration experiments.
Place, publisher, year, edition, pages
2002. Vol. 43, no 6, 1027-1029 p.
IdentifiersURN: urn:nbn:se:kth:diva-21316ISI: 000173851300026OAI: oai:DiVA.org:kth-21316DiVA: diva2:340014
QC 201005252010-08-102010-08-10Bibliographically approved