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Russian Chemical Bulletin

, 57:2364 | Cite as

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

  • K. V. Kudryavtsev
Full Articles

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 cycloaddition azomethine ylides pyrrolizidines multicomponent reactions 

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Copyright information

© Springer Science+Business Media, Inc.  2008

Authors and Affiliations

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

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