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.
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1 Introduction
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2 Synthesis of Pyrrolidinetrione Derivatives
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2.1 Pyrrolidine-2,3,5-trione Derivatives A, Substituted at C-4
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2.2 Pyrrolidine-2,3,5-trione Derivatives B with Exocyclic C = C at Position C-4
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2.3 Pyrrolidine-2-thioxo-4,5-dione Derivatives C
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2.4 Synthesis of Schiff Bases at C-6 of Pyrrolidine-2,3,5-trione Derivatives B and C
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2.5 Preparation of Pyrrolidine-2,3,4-trione Derivatives D
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3 Reactivity of Pyrrolidine-2,3,5-trione Derivatives
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3.1 Reactions of Pyrrolidine-2,3,5-triones with Monoamines
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3.2. Synthesis of Fused Heterocyclic Systems
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3.2.1 Reactions at C-3 and C-6 of Pyrrolidinetriones C
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3.2.2 Pyrrolo[3,4-c]pyrazole, pyrrolo[3,4-c]1,4-diazepine and Pyrrolo[3,4-f]1,5-diazocine
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3.3 Rearrangements and Ring Expansion of Pyrrolidinetrione Derivatives
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3.3.1 Furan-2,3-dione Derivatives
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3.3.2 Furo[3,4-c]pyridine Derivatives
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3.3.3 Pyrrolo[3,4-c]pyridine Derivatives
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3.3.4 Pyrroline-2,3-dione Derivatives
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3.3.5 Ring Expansion of Pyrrolidine-2,3,5-trione Derivatives to Quinoline Derivatives
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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
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3.5 Heterocyclisation of Pyrrolidine-2,3,5-triones with Bifunctional Nucleophiles
in Addition/Cyclization
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3.5.1 Synthesis of 1,3-Thiazine, Pyrimidine by Addition Reaction
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3.5.2 Reaction of Pyrrolidine-2,3,5-triones with Methylene-Active Compounds
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3.5.3 Reaction of Pyrrolidine-2,3,5-triones with Enaminocarbonyl Compounds
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3.5.4 Synthesis of 1,5-Benzodiazepine and 1,5-Benzothiazepine Derivatives
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3.5.5 4-Diazopyrrolidine-2,3,5-triones in the Synthesis of Pyrrolo[3.4-c]pyridazines
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3.6 Pyrrolidine-2,3,4-trione Derivatives in the Synthesis of Anellated Nitrogen-Containing
5,5-Ring Systems
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4 Hydrogenation of Pyrrolidine-2,3,5-triones
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5 Summary
pyrrolidinetrione - rearrangement - fused heterocyclic systems - hydrogenation - Schiff
bases
