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

Synthesis of Nitrogen-Containing Derivatives of (18 alpha, 19 beta)-19-Hydroxy-2,3-secooleanane-2,3,28-trioic Acid 28,19-Lactone Full article

Journal

Helvetica Chimica Acta
ISSN: 0018-019X , E-ISSN: 1522-2675

Output data

Year: 2013, Volume: 96, Number: 9, Pages: 1757-1781 Pages count : DOI: 10.1002/hlca.201200492

Tags

2; 3-Secotriterpenoids; Cyclic imides; Pyrrolidinetriones; Oxazolidinediones; Spiro compounds; Oxalyl chloride

Authors

Shernyukov Andrey V. ¹ , Mainagashev Ilya Ya. ¹ , Korchagina Dina V. ¹ , Genaev Alexander M. ¹ , Komarova Nina I. ¹ , Salakhutdinov Nariman F. ¹ , Tolstikov Genrikh A. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, RU-630090 Novosibirsk, Russia

The object of this study is the interaction of the cyclic anhydride 2 of (18,19)-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 (Scheme2), whereas the interaction with primary amines yielded a mixture of isomeric amides (Scheme10). 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 (Scheme4).

Shernyukov A.V. , Mainagashev I.Y. , Korchagina D.V. , Genaev A.M. , Komarova N.I. , Salakhutdinov N.F. , Tolstikov G.A.
Synthesis of Nitrogen-Containing Derivatives of (18 alpha, 19 beta)-19-Hydroxy-2,3-secooleanane-2,3,28-trioic Acid 28,19-Lactone
Helvetica Chimica Acta. 2013. V.96. N9. P.1757-1781. DOI: 10.1002/hlca.201200492 WOS Scopus РИНЦ

Published print:	Sep 1, 2013
Published online:	Sep 18, 2013

Web of science	WOS:000327864000011
Scopus	2-s2.0-84884971759
Elibrary	20454394
OpenAlex	W2034694507