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Synthesis 2001(6): 0811-0827
DOI: 10.1055/s-2001-13398
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Pyrrolidinetrione Derivatives: Synthesis And Applications in Heterocyclic Chemistry

Barbara Zaleska*, Sławomir Lis
Department of Organic Chemistry, Jagiellonian University Kraków, ul. Ingardena 3, 30-060 Kraków, Poland
Fax: +48(1)26340515; e-Mail: zaleska@chemia.uj.edu.pl;
Further Information

Publication History

Received 7 February 2001
Publication Date:
15 October 2004 (online)

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Abstract

This review article, covering the literature from 1891 to 1999, deals with the methods of preparation of pyrrolidinetrione derivatives, emphasis being placed on methods of reasonable efficiency. A general applicability of these compounds as versatile building blocks in synthesis of fused heterocyclic systems is in focus.

  • 1 Introduction

  • 2 Synthesis of Pyrrolidinetrione Derivatives

  • 2.1 Pyrrolidine-2,3,5-trione Derivatives A, Substituted at C-4

  • 2.2 Pyrrolidine-2,3,5-trione Derivatives B with Exocyclic C = C at Position C-4

  • 2.3 Pyrrolidine-2-thioxo-4,5-dione Derivatives C

  • 2.4 Synthesis of Schiff Bases at C-6 of Pyrrolidine-2,3,5-trione Derivatives B and C

  • 2.5 Preparation of Pyrrolidine-2,3,4-trione Derivatives D

  • 3 Reactivity of Pyrrolidine-2,3,5-trione Derivatives

  • 3.1 Reactions of Pyrrolidine-2,3,5-triones with Monoamines

  • 3.2. Synthesis of Fused Heterocyclic Systems

  • 3.2.1 Reactions at C-3 and C-6 of Pyrrolidinetriones C

  • 3.2.2 Pyrrolo[3,4-c]pyrazole, pyrrolo[3,4-c]1,4-diazepine and Pyrrolo[3,4-f]1,5-diazocine

  • 3.3 Rearrangements and Ring Expansion of Pyrrolidinetrione Derivatives

  • 3.3.1 Furan-2,3-dione Derivatives

  • 3.3.2 Furo[3,4-c]pyridine Derivatives

  • 3.3.3 Pyrrolo[3,4-c]pyridine Derivatives

  • 3.3.4 Pyrroline-2,3-dione Derivatives

  • 3.3.5 Ring Expansion of Pyrrolidine-2,3,5-trione Derivatives to Quinoline Derivatives

  • 3.4 Pyrrolidine-2,3,5-triones in the Synthesis of Quinoxaline, Benzoxazine, Cyclopentanone and 1,2,4-Triazine Derivatives by Cyclocondensation at C-2 and C-3

  • 3.5 Heterocyclisation of Pyrrolidine-2,3,5-triones with Bifunctional Nucleophiles in Addition/Cyclization

  • 3.5.1 Synthesis of 1,3-Thiazine, Pyrimidine by Addition Reaction

  • 3.5.2 Reaction of Pyrrolidine-2,3,5-triones with Methylene-Active Compounds

  • 3.5.3 Reaction of Pyrrolidine-2,3,5-triones with Enaminocarbonyl Compounds

  • 3.5.4 Synthesis of 1,5-Benzodiazepine and 1,5-Benzothiazepine Derivatives

  • 3.5.5 4-Diazopyrrolidine-2,3,5-triones in the Synthesis of Pyrrolo[3.4-c]pyridazines

  • 3.6 Pyrrolidine-2,3,4-trione Derivatives in the Synthesis of Anellated Nitrogen-Containing 5,5-Ring Systems

  • 4 Hydrogenation of Pyrrolidine-2,3,5-triones

  • 5 Summary

Key words

pyrrolidinetrione - rearrangement - fused heterocyclic systems - hydrogenation - Schiff bases

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Deutsche Gold und Silver Scheidanstalt, Neth. Appl. 298,715, 1965; Ger. Appl., 1962.

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Zaleska, B.; Lech, J.; in press.