Russian Chemical Bulletin

, 57:2364

Three-component synthesis of tricyclic lactams containing the pyrrolizidin-3-one moiety

Full Articles

DOI: 10.1007/s11172-008-0337-8

Cite this article as:
Kudryavtsev, K.V. Russ Chem Bull (2008) 57: 2364. doi:10.1007/s11172-008-0337-8

Abstract

Tricyclic lactams containing the pyrrolizidin-3-one moiety were synthesized by the three-component reaction of aromatic aldehydes, glutamic acid (or glutamine), and N-methylmaleimide. The cascade reactions involve the stereospecific generation of azomethine ylides, the 1,3-dipolar endo- and exo-cycloaddition of a dipolarophile to the ylides, and the lactamization and afford two series of stereoisomeric pyrrolizidin-3-ones. The alkaline hydrolysis of the products of the mulitcomponent reaction gives oxopyrrolizidinedicarboxylic acid derivatives.

Key words

1,3-dipolar cycloadditionazomethine ylidespyrrolizidinesmulticomponent reactions

Copyright information

© Springer Science+Business Media, Inc.  2008

Authors and Affiliations

  1. 1.Department of ChemistryM. V. Lomonosov Moscow State UniversityMoscowRussian Federation