Synthesis of Nitrogen-Containing Derivatives of (18α,19β)-19-Hydroxy-2,3-secooleanane-2,3,28-trioic Acid 28,19-Lactone

The object of this study is the interaction of the cyclic anhydride 2 of (18α,19β)‐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 s...

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Published in:Helvetica chimica acta 2013-09, Vol.96 (9), p.1757-1781
Main Authors: Shernyukov, Andrey V., Mainagashev, Ilya Ya, Korchagina, Dina V., Genaev, Alexander M., Komarova, Nina I., Salakhutdinov, Nariman F., Tolstikov, Genrikh A.
Format: Article
Language:English
Subjects:
2,3‐Secotriterpenoids
3-Secotriterpenoids
Cyclic imides
Oxalyl chloride
Oxazolidinediones
Pyrrolidinetriones
Spiro compounds
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Summary:The object of this study is the interaction of the cyclic anhydride 2 of (18α,19β)‐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).
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201200492