3-Pyrrolidinones: Michael Addition and Schmidt Rearrangement Reactions

Amer, F. A.; Hammouda, M.; El-Ahl, A. A. S.; Abdel‐Wahab, Bakr F.

doi:10.1080/00397910802378373

Cited by 10 publications

(2 citation statements)

References 10 publications

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“…The title compound (I) was investigated owing to the biological activities exhibited pyrroles and pyranopyrrole analogues (Amer et al 2009;Amer et al 2008). Herein, its crystal structure determination is described.…”

Section: S1 Commentmentioning

confidence: 99%

4-Dimethylamino-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

et al. 2013

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Section: S1 Commentmentioning

confidence: 99%

4-Dimethylamino-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

et al. 2013

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“…4-cyano-pyrrolidin-3-ones [11,12] are particularly interesting precursors for synthesis of pyrrolidines. Considering the fact that they have two electrophilic sites, enriches their chemical reactivity and led to generating novel compounds [11], [13][14][15][16] of promising biological activity. [16] Based on the literature survey and as a part of our growing interest in preparing new organophosphorus compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and antimicrobial activity of novel pyrrolidine-3-carbonitrile derivatives,

2018

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NEWLY synthesized pyrrolidine-3-carbonitrile derivatives were evaluated as antimicrobial activity. The structures of these derivatives were derived from reactions of 1-(4-methoxyphenyl)-4-oxopyrrolidine-3-carbonitrile (1) with the stabilized phosphorus ylides, Wittig-Horner reagents, trialkylphosphites, as well as tris(dialkylamino)phosphines. The antimicrobial activity of the synthesized compounds was evaluated against Gram positive, Gram negative bacteria and fungi. The results showed comparable antibiotic activity to the reference antibiotic compound used in the study.

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The Schmidt Reaction

et al. 2012

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The classical form of the Schmidt reaction involves the reaction of a carbon‐centered electrophile with hydrazoic acid with loss of nitrogen, usually with a rearrangement that forms a new carbon‐nitrogen bond. Although the conversion of a ketone into an amide is the most commonly used variation, mechanistically related versions utilize an aldehyde, acid, or a carbocation generated from an alkene or alcohol as the electrophilic component. In recent years, the definition of the Schmidt reaction has been modified to include analogous reactions in which the hydrazoic acid is replaced by an alkyl azide, promoted by Lewis acids. The use of an alkyl azide uniquely permits the formulation of intramolecular Schmidt reactions of the azide with a carbonyl or carbocationic electrophile.

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3-Pyrrolidinones: Michael Addition and Schmidt Rearrangement Reactions

Cited by 10 publications

References 10 publications

4-Dimethylamino-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

4-Dimethylamino-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

Synthesis, Characterization and antimicrobial activity of novel pyrrolidine-3-carbonitrile derivatives,

The Schmidt Reaction

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