Synthesis of novel multi-functionalized pyrrolidines by [3 + 2] dipolar cycloaddition of azomethine ylides and vinyl ketones

Pešić, Marko; Bugarinović, Jovana P.; Minić, Aleksandra; Komatina, Danijela Ilić; Pejović, Anka; Šmit, Biljana; Stevanović, Dragana; Damljanović, Ivan

doi:10.1007/s00706-018-2340-6

Cited by 4 publications

(7 citation statements)

References 105 publications

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“…This methodology proved to be quite useful affording pure products in good yields, within a short reaction time. 8 Synthetic principle has been depicted in Scheme 1. The common procedure consists of two phases that were taken out consecutively.…”

Section: Resultsmentioning

confidence: 99%

“…All reactions afforded targeted pyrrolidines 3a-l, but yields were significantly lower than it was reported earlier. 8 In order to increase yields, the reaction time was extended, and better outcomes were reached after 90 min of stirring. However, further elongation of the reaction time did not show expected improvement.…”

Section: Resultsmentioning

confidence: 99%

“…α-Imino esters (1a-f) were prepared according to literature. 8 Enones (2a and 2b) were prepared by slightly modified previously described procedure. 9 All reactions were monitored by thin-layer chromatography (TLC) on Silica gel 60 F254 precoated Al foils (200 μm layer thickness, Sigma-Aldrich).…”

Section: Methodsmentioning

confidence: 99%

“…General procedure for the syntheses of a-imino esters.-The αimino esters (1a-f) were prepared by a slight modification of the reported procedure. 8 The anhydrous sodium sulfate (71 mg, 0.5 mmol, 2 equiv.) and Et 3 N (28 mg, 0.27 mmol, 1.1 equiv.)…”

Section: Methodsmentioning

confidence: 99%

“…7 We have recently described a brief methodology for the synthesis of the substituted pyrrolidines using 1,3-dipolar cycloaddition of azomethine ylides. 8 Our long-term interest also comprises the synthesis of bioactive ferrocene compounds, commonly by a formal substitution of an aromatic fragment of the known bioactive derivative by ferrocene moiety. To the best of our knowledge, ferrocene-substituted chalcones have never been submitted to the reaction with azomethine ylides.…”

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confidence: 99%

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Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines

Pešić

Bugarinović

Minić

et al. 2020

J. Electrochem. Soc.

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The design, synthesis, spectral and electrochemical characterization of a series of novel pyrrolidine derivatives have been described. The synthesis was achieved by 1,3-dipolar cycloaddition of azomethine ylides and ferrocene-substituted chalcones, while detailed characterization of the compounds was performed by IR, NMR and elemental analyses, followed by X-ray diffraction experiment for one representative. The electrochemical properties of obtained ferrocene-containing heterocycles were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. DNA-binding capacity of all products was studied using CV and DPV, highlighting a derivative with five times better binding affinity than the others. DFT calculations and molecular docking studies were carried out to gain more exhaustive insight into the type of interactions of the distinguished compound and the nucleic acid.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines

Pešić

Bugarinović

Minić

et al. 2020

J. Electrochem. Soc.

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Addition Reactions: Cycloaddition

Dennis¹

2023

Organic Reaction Mechanisms Series

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Recent Advances in Radical Coupling Strategies Enabled by 2‐Azaallyl Anions as Super‐Electron‐Donors

Zou.,

Wang,

Ying

2024

Adv Synth Catal

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Abstract. Due to amine derivatives widely existing in numerous clinical medicines and bioactive compounds, their synthesis has received considerable attention over the past few decades. Traditional methods for the synthesis of amine derivatives largely relied on the reduction of nitroarenes, amides, hydrazines, nitriles, and azides. Recently, the discovery of 2‐azaallyl anions as super‐electron‐donors (SEDs) has opened up new possibilities for the construction of diverse carbon−carbon and carbon−heteroatom bonds through radical coupling strategies. This breakthrough highlights the potential of generating 2‐azaallyl radicals as versatile intermediates in organic synthesis. Then, hydrolysis of the coupling product can easily separate the corresponding amine derivatives. Thus, tremendous attention has been paid to the C–H functionalization of 2‐azaallyls as an alternative strategy for the synthesis of amine derivatives. Herein, we comprehensively summarize the recent progress in radical coupling strategies enabled by 2‐azaallyl anions as SEDs. Their proposed mechanistic pathways, advantages, and limitations are also discussed in detail.

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Synthesis of novel multi-functionalized pyrrolidines by [3 + 2] dipolar cycloaddition of azomethine ylides and vinyl ketones

Cited by 4 publications

References 105 publications

Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines

Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines

Addition Reactions: Cycloaddition

Recent Advances in Radical Coupling Strategies Enabled by 2‐Azaallyl Anions as Super‐Electron‐Donors

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