Nitropyridines as 2π-Partners in 1,3-Dipolar Cycloadditions with N-Methyl Azomethine Ylide: An Easy Access to Condensed Pyrrolines [PDF]
Molecules, 2021 1,3-Dipolar cycloaddition reactions of 2-substituted 5-R-3-nitropyridines and isomeric 3-R-5-nitropyridines with N-methyl azomethine ylide were studied. The effect of the substituent at positions 2 and 5 of the pyridine ring on the possibility of the [3 ...
Maxim A. Bastrakov +3 more
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Ethyl 1-benzyl-1,2,3,3a,4,10b-hexahydropyrrolo[2′,3′:3,4]pyrrolo[1,2-a]benzimidazole-2-carboxylate [PDF]
Acta Crystallographica Section E, 2011 The title molecule, C22H23N3O2, was obtained via an intramolecular cycloaddition of an azomethine ylide and an alkene tethered by a benzimidazole unit. The benzoimidazole unit is essentially planar, with an r.m.s. deviation of 0.0087 Å
Liping Meng +2 more
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Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple [PDF]
Beilstein Journal of Organic Chemistry, 2022 A reliable method for the synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexanes through the 1,3-dipolar cycloaddition (1,3-DC) reactions of cyclopropenes to the stable azomethine ylide – protonated form of Ruhemann's purple (PRP) has ...
Alexander S. Filatov +4 more
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Recent Developments in Azomethine Ylide-Initiated Double Cycloadditions [PDF]
MoleculesAzomethine ylides (AMYs) have a nitrogen–carbon double bond and an electron lone pair on the nitrogen atom. They are essential 1,3-dipoles for [3+2] cycloadditions in the synthesis of pyrrolidine-containing heterocycles.
Tieli Zhou +4 more
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Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling [PDF]
Nature Communications, 2017 Polyaromatic hydrocarbons can be precisely manipulated to yield ever more complex and discrete graphene analogs, such as nanographenes. Here, the authors use azomethine ylide homocoupling to insert an antiaromatic pyrazine ring into the core of a ...
Xiao-Ye Wang +15 more
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A Molecular Electron Density Theory Study of the [3+2] Cycloaddition Reaction of an Azomethine Ylide with an Electrophilic Ethylene Linked to Triazole and Ferrocene Units [PDF]
Molecules, 2022 The [3+2] cycloaddition (32CA) reaction of an azomethine ylide (AY) with an electrophilic ethylene linked to triazole and ferrocene units has been studied within the Molecular Electron Density Theory (MEDT) at the ωB97X-D/6-311G(d,p) level.
Luis R. Domingo +2 more
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Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates. [PDF]
J Org Chem, 2013 We have performed a combined computational and experimental study to elucidate the mechanism of a metal-free α-amination of secondary amines. Calculations predicted azaquinone methides and azomethine ylides as the reactive intermediates and showed that ...
Dieckmann A +5 more
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Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds
Molecules, 2023 Azomethine ylides are nitrogen-based three-atom components commonly used in [3+2]-cycloaddition reactions with various unsaturated 2π-electron components.
Siva S. Panda +3 more
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Unexpected Course of Reaction Between (1E,3E)-1,4-Dinitro-1,3-butadiene and N-Methyl Azomethine Ylide—A Comprehensive Experimental and Quantum-Chemical Study [PDF]
MoleculesIn recent times, interest in the chemistry of conjugated nitrodienes is still significantly increasing. In particular, the application of these compounds as building blocks to obtain heterocycles is a popular object of research.
Mikołaj Sadowski, Karolina Kula
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Topological classification of cycloadditions occurring on-surface and in the solid-state [PDF]
Communications ChemistryThe study of cycloaddition mechanisms is central to the fabrication of extended sp 2 carbon nanostructures such as graphene nanoribbons and spin chains. Reaction modeling in this context has focused mostly on putative, energetically preferred, exothermic
Juan Li +15 more
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