Preparation of conjugated nitroalkenes: short review

Zawadzińska, Karolina; Gaurav, Gajendra Kumar; Jasiński, Radomir

doi:10.58332/v22i1a05

Cited by 11 publications

(5 citation statements)

References 62 publications

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“…Z-C-(3-pyridyl)-N-methylnitrone (1) was prepared via condensation of a 3-pyridyl aldehyde with the methylhydroxylamine in an etanolic solution according to the already known procedure [37]. Conjugated nitroalkenes were prepared from respective nitroalco-hols via respective nitroalkyl esters according to protocols described in the literature [38][39][40]. Commercially available (Sigma-Aldrich Poland, Merck Poland) reagents and solvents were used in all experiments.…”

Section: Methodsmentioning

confidence: 99%

Full Regio- and Stereoselective Protocol for the Synthesis of New Nicotinoids via Cycloaddition Processes with the Participation of Trans-Substituted Nitroethenes: Comprehensive Experimental and MEDT Study

et al. 2023

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[3 + 2] Cycloaddition reactions with the participation of Z-C-(3-pyridyl)-N-methylnitrone and series of E-2-R-nitroethenes were both experimentally and theoretically explored in the framework of Molecular Electron Density Theory. It was found that all considered processes are realized under mild conditions and in full regio- and stereocontrol. The ELF analysis additionally showed that the studied reaction proceeds by a two-stage, one-step mechanism.

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Section: Methodsmentioning

confidence: 99%

Full Regio- and Stereoselective Protocol for the Synthesis of New Nicotinoids via Cycloaddition Processes with the Participation of Trans-Substituted Nitroethenes: Comprehensive Experimental and MEDT Study

et al. 2023

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“…This topic is presented in many review articles and even books. The discussed subjects include the synthesis [1][2] and biological properties of CNAs, [3][4] as well as aspects of their chemical transformations, both of synthetic means [5][6][7][8] and based on quantum-chemistry. [9][10][11][12][13] CNAs are an attractive building block widely used in the modern organic chemistry for synthesis carbo-and heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

Nitro-functionalized analogues of 1,3-Butadiene: An overview of characteristic, synthesis, chemical transformations and biological activity

Sadowski,

Kula

2024

10.5267/j.ccl

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The nitrovinyl moiety is surely one of the most reactive fragments in organic chemistry, continuously employed to explore original pathways and reach new targets. One of the most important classes of chemicals containing this fragment are nitro-functionalised analogues of 1,3-butadiene. In this paper a comprehensive review study of these compounds is performed. The manuscript includes an analysis of physicochemical properties, spectral characteristic, synthesis, biological activity, and possible transformations of nitro substituted analogues of 1,3-butadiene. The analysis was divided into several parts, depending on the number of nitro groups included in the structure of a 1,3-butadiene analogue. In addition, the work includes information about hazards and safety principles when working with nitro compounds. Based on the analysis of the literature, it can be concluded that nitro-functionalised analogues of 1,3-butadiene exhibit diversified profile of properties, and an outstanding potential as valuable reagents in organic synthesis useful to obtain heterocycles that can be applied in medicine.

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“…Thanks to this, it is possible to synthesize many nitrogen-containing connections like amines, hydroxylamines, oximes, nitriles, diazocompounds and others as well as to obtain carbonyl compounds [2]. Among all nitro compounds, a class of conjugated nitroalkenes (CNAs) deserves special attention [3,4]. These compounds exhibit various biological activities such as antibacterial [5,6] or antifungal [7].…”

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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Preparation of conjugated nitroalkenes: short review

Cited by 11 publications

References 62 publications

Full Regio- and Stereoselective Protocol for the Synthesis of New Nicotinoids via Cycloaddition Processes with the Participation of Trans-Substituted Nitroethenes: Comprehensive Experimental and MEDT Study

Full Regio- and Stereoselective Protocol for the Synthesis of New Nicotinoids via Cycloaddition Processes with the Participation of Trans-Substituted Nitroethenes: Comprehensive Experimental and MEDT Study

Nitro-functionalized analogues of 1,3-Butadiene: An overview of characteristic, synthesis, chemical transformations and biological activity

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

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