Acyl transfer of 8-acetoxy-2-oxazolinylquinoline assisted by hydrogen bonding formation
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- Authors:
- Hortala, Laurent
Moberg, Christina
Levacher, Vincent
Bourguignon, Jean
Dupas, Georges - Source:
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Feb2002, Vol. 43 Issue 6, p1027. 3p. - Publication Date:
- 2002-02-04
- Language:
- English
- Abstract:
- 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. [Copyright &y& Elsevier]
- Subjects:
- ACYLATION
QUINOLINE
AMINES
HYDROGEN bonding - Format:
- Academic Journal
- DOI:
- 10.1016/S0040-4039(01)02329-2
- Database:
- Academic Search Premier
- Journal:
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Volume:
- 43
- Issue:
- 6
- Page Start:
- 1027
- Page Count:
- 3
- ISSN:
- 00404039
