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
Abstract:[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.
“…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 ].…”
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.
“…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 ].…”
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.
“…Considering the broad applicational potential of nitrones, their synthesis seems an interesting field of development. Furthermore, nitrones of C-(pyrid-3-yl) type can be, and have successfully been, used in synthesis of nicotine analogues [6,7]. Those nicotine analogues can be useful in industry [8].…”
In this work, new nitrones, derived from nicotinaldehyde and N-aryl-N-hydroxylamines are described, and methods for their synthesis, and purification are presented. Spectral characterisation of said nitrones is also presented.
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