Understanding the Molecular Mechanism of Thermal and LA-Catalysed Diels–Alder Reactions between Cyclopentadiene and Isopropyl 3-Nitroprop-2-Enate

Dresler, Ewa; Wróblewska, Aneta; Jasiński, Radomir

doi:10.3390/molecules28145289

Cited by 5 publications

(3 citation statements)

References 49 publications

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“…Analysis of the electronic properties of organic molecules is an important and universal tool for predicting their reactivity [67][68][69]. This approach was recently and successfully applied to interpret the reactivity of different types of molecular segments and the course of many bimolecular organic processes [70][71][72][73][74].…”

Section: Power Of the Global And Local Interactions In The Context Of...mentioning

confidence: 99%

“…The regiodirection of the considered reaction is predominantly determined by steric repulsion involving the germinal methyl groups derived from the isobutene molecule. In contrast, analogous 32CAs involving electron-rich nitrile N-oxides and electrophilic alkenes are fully determined by the nature of global and local electronic interactions [23,24,70].…”

Section: Exploration Of Reaction Profilesmentioning

confidence: 99%

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Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study

Dresler,

Wróblewska,

Jasiński

2024

Molecules

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Regioselectivity and the molecular mechanism of the [3+2] cycloaddition reaction between nitro-substituted formonitrile N-oxide 1 and electron-rich alkenes were explored on the basis of the wb97xd/6-311+G(d) (PCM) quantum chemical calculations. It was established that the thermodynamic factors allow for the formation of stable cycloadducts along all considered models. The analysis of the kinetic parameters of the main processes show that all [3+2] cycloadditions should be realized with full regioselectivity. In all cases, the formation of 5-substituted 3-nitro-2-isoxazolidines is clearly preferred. It is interesting that regiodirection is not determined by the local electrophile/nucleophile interactions but by steric effects. From a mechanistic point of view, all considered reactions should be treated as polar, one-step reactions. All attempts to locate the hypothetical zwitterionic intermediates along the cycloaddition paths were, however, not successful.

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Section: Power Of the Global And Local Interactions In The Context Of...mentioning

confidence: 99%

Section: Exploration Of Reaction Profilesmentioning

confidence: 99%

Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study

Dresler,

Wróblewska,

Jasiński

2024

Molecules

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“…These compounds exhibit various biological activities such as antibacterial [ 5 , 6 ] or antifungal [ 7 ]. This makes CNAs often used in many reactions such as Michael addition [ 8 , 9 ] as well as cycloaddition (CA) reactions, to synthesize heterocycles, especially for the preparation of five-membered rings [ 10 ] like pyrazolines [ 11 , 12 ], isoxazolines [ 13 , 14 , 15 , 16 ] or pyrrolidine [ 17 , 18 ], and six-membered rings in the Diels-Alder reaction [ 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

(1E,3E)-1,4-Dinitro-1,3-butadiene—Synthesis, Spectral Characteristics and Computational Study Based on MEDT, ADME and PASS Simulation

Sadowski,

Synkiewicz-Musialska,

Kula

2024

Molecules

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The chemistry of conjugated nitrodienes is becoming increasingly popular. These molecules are successfully applied in cycloaddition to synthesize six-membered rings in Diels-Alder reactions. Nitrodienes can be also applied to obtain bis-compounds in [3+2] cycloaddition. Moreover, the presence of a nitro group in the structure provides a possibility of further modification of the products. The simplest symmetrical representative of conjugated nitrodienes is (1E,3E)-1,4-dinitro-1,3-butadiene. Although the first mentions of the compound date back to the early 1950s, the compound has not yet been examined thoroughly enough. Therefore, in this article, a comprehensive study of (1E,3E)-1,4-dinitro-1,3-butadiene has been described. For this purpose, an experimental study including the synthesis process as well as an evaluation of the spectral characteristics has been conducted. So as to better understand the properties of this compound, a computational study of reactivity indices based on MEDT and also an assessment of pharmacokinetics and biological activity according to ADME and PASS methodologies have been made. On this basis, some future application trends of (1E,3E)-1,4-dinitro-1,3-butadiene have been proposed.

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ADME Study, Molecular Docking, Elucidating the Selectivities and the Mechanism of [4 + 2] Cycloaddition Reaction Between (E)-N ((dimethylamino)methylene)benzothioamide and (S)-3-acryloyl-4-phenyloxazolidin-2-one

Atif,

Barhoumi,

Syed

et al. 2024

Mol Biotechnol

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Understanding the Molecular Mechanism of Thermal and LA-Catalysed Diels–Alder Reactions between Cyclopentadiene and Isopropyl 3-Nitroprop-2-Enate

Cited by 5 publications

References 49 publications

Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study

Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study

(1E,3E)-1,4-Dinitro-1,3-butadiene—Synthesis, Spectral Characteristics and Computational Study Based on MEDT, ADME and PASS Simulation

ADME Study, Molecular Docking, Elucidating the Selectivities and the Mechanism of [4 + 2] Cycloaddition Reaction Between (E)-N ((dimethylamino)methylene)benzothioamide and (S)-3-acryloyl-4-phenyloxazolidin-2-one

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