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Synthesis of Nitrogen-Containing Derivatives of (18 α,19 β)-19-Hydroxy-2,3-secooleanane-2,3,28-trioic Acid 28,19-Lactone.
- Source :
-
Helvetica Chimica Acta . Sep2013, Vol. 96 Issue 9, p1757-1781. 25p. - Publication Year :
- 2013
-
Abstract
- The object of this study is the interaction of the cyclic anhydride 2 of (18 α,19 β)-19-hydroxy-2,3-secooleanane-2,3,28-trioic acid 28,19-lactone ( 1) with primary and secondary amines. It was shown that the products of steric control (the corresponding 2-amino-2-oxo-3-oic acids=2-amides) were formed solely upon the opening of the anhydride cycle by secondary amines ( Scheme 2), whereas the interaction with primary amines yielded a mixture of isomeric amides ( Scheme 10). In the latter case, the solvent provided a noticeable effect on the reaction selectivity, which was demonstrated in the case of 4-methoxybenzylamine. The interaction between the resulting 3-amides and oxalyl chloride yielded the corresponding cyclic imides, whereas under these conditions, 2-amides formed spiropyrrolidinetriones ( Scheme 4). [ABSTRACT FROM AUTHOR]
- Subjects :
- *NITROGEN
*HYDROXY acids
*LACTONES
*AMINES
*ANHYDRIDES
*CHEMICAL derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 0018019X
- Volume :
- 96
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Helvetica Chimica Acta
- Publication Type :
- Academic Journal
- Accession number :
- 90469402
- Full Text :
- https://doi.org/10.1002/hlca.201200492