Pyrrolidinetrione Derivatives: Synthesis And Applications in Heterocyclic Chemistry

Zaleska, Barbara; Lis, S.

doi:10.1055/s-2001-13398

Cited by 10 publications

(3 citation statements)

References 43 publications

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“…Carbon atoms of oxo groups capable of involvement in enolization and intramolecular hydrogen bond formation are significantly more unshielded. There is a confirmation of this phenomenon for 2,4,5-trioxopyrrolidines in reported data. − In the case of (2 E, 5 Z )- 3a – 3f conformation, the downfield shift of the C3′ carbonyl group signal can be explained by the low probability of NH···OC3′ intramolecular hydrogen bond formation and enolization. Consequently, the upfield signal was assigned to the C3′ carbonyl group of (2 Z, 5 Z )- 3a – 3f conformation.…”

Section: Resultsmentioning

confidence: 56%

Discovery of Methyl (5Z)-[2-(2,4,5-Trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetates as Antifungal Agents against Potato Diseases

Обыденнов

Хамидуллина

Galushchinskiy

et al. 2018

J. Agric. Food Chem.

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Synthesis, isomerism, and fungicidal activity against potato diseases of new (5 Z)-[2-(2,4,5-trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetate derivatives with 1,3-thiazolidine-4-one and pyrrolidine-2,3,5-trione moieties linked by an exocyclic C═C bond were described. Their structures were clearly confirmed by spectroscopic and spectrometric data (Fourier transform infrared spectroscopy, H andC nuclear magnetic resonance, and mass spectrometry), elemental analysis, and X-ray diffraction crystallography. A bioassay for antifungal activity in vitro against Phytophthora infestans, Fusariun solani, Alternaria solani, Rhizoctonia solani, and Colletotrichum coccodes demonstrated that 2,4,5-trioxopyrrolidin-1,3-thiazolidine derivatives exhibited a relatively broad spectrum of antifungal activity. One of the compounds showed considerable activity against all of the strains; in the case of F. solani, P. infestans, and A. solani, it possesses comparable or better fungicidal efficacy than the positive control Consento. Consequently, this compound is a promising fungicidal candidate for plant protection.

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Section: Resultsmentioning

confidence: 56%

Discovery of Methyl (5Z)-[2-(2,4,5-Trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetates as Antifungal Agents against Potato Diseases

Обыденнов

Хамидуллина

Galushchinskiy

et al. 2018

J. Agric. Food Chem.

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“…Synthesis of N-alkyl imides was usually accomplished by the reaction of imides with alkyl halides in the presence of a base, such as sodium hydride [13,14], triethylamine [15], KF/Al 2 O 3 [6], an organometallic compound (e.g., butyllithium) [16], K 2 CO 3 [17][18][19][20][21][22], Na 2 CO 3 [23,24], Cs 2 CO 3 [25,26], potassium hydroxide [27] or sodium amide [28]. The reactions were carried out in various solvents, such as acetone [17,18,26,29], DMSO [26], DMF [23,26,30], THF [26], CH 3 CN [6,22,25,26,31], xylene [22,32], butan-2-one [19], benzene [20,26], ionic liquids [27,33], or in the presence of excess alkylating agent [17,34].…”

Section: Introductionmentioning

confidence: 99%

N‐Alkylation of imides using phase transfer catalysts under solvent‐free conditions

Jaśkowska

Kowalski

2008

Journal of Heterocyclic Chem

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48-94%Solvent-free N-Alkylation of imides in the reaction of imides and alkylhalides, catalyzed by PT catalysts under solvent-free conditions, has been developed. The reaction occurs in the presence of K 2 CO 3 , and in many cases it takes place spontaneously. In the N-benzylation reaction, it has been recognized that TBAB (tetrabutylammonium bromide) and TBATFB (tetrabutylammonium tetrafluoroborate) show highest catalytic effect. Versatility and synthetic capacity of the solvent-free alkylation has been confirmed by Nbenzylation and N-ethylation of various imides. The developed procedure gives easy access to N-( -bromoalkyl)imides.

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“…26 The use of pyrrolidine-2,3,5-trione (1) in our synthesis of expected pharmacologically active fused pyrrolo [2,3-b]quinoxaline system enables insertion of an additional carbonyl group, which may facilitate linkage with receptors. 26 The use of pyrrolidine-2,3,5-trione (1) in our synthesis of expected pharmacologically active fused pyrrolo [2,3-b]quinoxaline system enables insertion of an additional carbonyl group, which may facilitate linkage with receptors.…”

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confidence: 99%

Synthesis and NMR Structural Assignment of 3-Benzoylpyrrolo- [2,3-b]quinoxalin-2(4H)-ones

Ostrowska¹,

Zylewski²,

Walocha³

2002

HETEROCYCLES

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A series of 3-benzoylpyrrolo[2,3-b]quinoxalin-2(4H)-ones, potential bioactive compounds have been synthesized. Their preparation is based on the efficient, regiospecific condensation of o-phenylenediamine with pyrrolidine-2,3,5-trione (1) or its enaminone derivatives, respectively, affording two polymorphic forms of the latter in solid. The NMR spectral assignment of 3benzoylpyrrolo[2,3-b]quinoxalin-2(4H)-ones confirms the presence of only one isomer with enaminone moiety in solution.The quinoxaline-peptide antibiotic family including echinomycin, 1 levomycin and actinoleucin 2 or pyrroloquinoxaline 3, 4 system contains one or more quinoxaline rings, structural unit of several bioactive compounds, exhibiting properties of various types such as antiviral, antibacterial, antifungal, insecticidal and cytotoxic. 5 Synthesis of the pyrrolo[2,3-b]quinoxaline system has been extensively investigated due to a potential pharmacological activity. Its synthesis is readily accomplished by the annelation of ophenylenediamine with 3-chloropyrrolidine-2-one, 6-13 4-oxa-2,10-diazabenzo[b]azulene-1,3,9-trione 14 or pyrrole-2,3-dione 15-21 derivatives, and 3-aminoquinoxaline derivative with diethyl carbonate, 22 respectively.1-Phenyl-4-phenylhydroxymethylidenepyrrolidine-2,3,5-trione (1), 23 used as a building block in our previous investigations on the synthesis of pyrrolo[3,4-x]diazacycloalkadiene 24,25 system, possesses αdicarbonyl moiety susceptible to the double nucleophilic attack, thus seems to be a convenient starting material in the synthesis of the new potential bioactive pyrrolo[2,3-b]quinoxaline derivatives. It is *Dedicated to memory of late Prof. Dr. hab. Wanda Żankowska-Jasińska

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Pyrrolidinetrione Derivatives: Synthesis And Applications in Heterocyclic Chemistry

Cited by 10 publications

References 43 publications

Discovery of Methyl (5Z)-[2-(2,4,5-Trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetates as Antifungal Agents against Potato Diseases

Discovery of Methyl (5Z)-[2-(2,4,5-Trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetates as Antifungal Agents against Potato Diseases

N‐Alkylation of imides using phase transfer catalysts under solvent‐free conditions

Synthesis and NMR Structural Assignment of 3-Benzoylpyrrolo- [2,3-b]quinoxalin-2(4H)-ones

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