Nitropyridines 11. *Recyclization of quaternary nitropyridinium salts into substituted nitroanilines

Garkushenko, A. K.; Poendaev, N. V.; Воронцова, М. А.; Сагитуллина, Г. П.

doi:10.1007/s10593-011-0783-3

Cited by 7 publications

(1 citation statement)

References 16 publications

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“…Ionic opening of A leads to the open‐chain form of B and C in which the cyclononene fragment rests in an equilibrium between the cis ‐ and trans ‐forms. Cyclization of the open‐chained form of C in [6]metacyclophane 3d takes place by intramolecular aldol‐crotonic condensation of the resulting formyl group with the methylene group of the polymethylene chain …”

Section: Resultsmentioning

confidence: 99%

[6]–[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy

et al. 2017

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Metacyclophanes have been developed as non‐planar aromatic compounds with unusual physical properties. [6]–[9]Metacyclophanes were synthesized by rearrangement of 3‐nitro(perhydrocycloalka)[b]pyridinium salts, and analysis of their spectroscopic data and X‐ray diffraction patterns indicates the aromaticity and flexibility of their benzene rings. The effectiveness and simplicity of the synthesis makes it possible to use them as available precursors in the synthesis of retinoids, indolophanes, and carbazolophanes.

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Section: Resultsmentioning

confidence: 99%

[6]–[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy

et al. 2017

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C₆‐Selective Direct Arylation of 2‐Phenylpyridine via an Activated N‐methylpyridinium Salt: A Combined Experimental and Theoretical Study

Yin

Zhong

et al. 2018

Adv Synth Catal

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An elegant pre‐activation strategy, based on the formation of N‐methylpyridinium iodide salts for C6‐selective direct arylation of 2‐phenylpyridines using Pd/Cu cooperative catalysis, has been developed. By this methodology, a wide range of unsymmetrical 2, 6‐diarylpyridines were synthesized with high reactivity and regioselectivity as well as good functional group tolerance. In particular, challenging substrates bearing electron donating groups (EDGs), such as OMe, NMe2, were also successfully employed in this reaction. Deuterium incorporation studies revealed that the C−H bond acidity is improved significantly in N‐methylpyridinium salts compared with their N‐Oxide and N‐iminopyridinium ylide counterparts, thus solving the long‐standing problem associated with previous strategies for the synthesis of diaryl pyridines. Finally, the control experiments and DFT calculations supported a Pd‐catalyzed and Cu‐mediated mechanism in which a carbenoid copper species that is formed in‐situ from N‐methylpyridinium salts, participates in a Pd‐catalyzed arylation followed by an iodide‐promoted N‐demethylation process.magnified image

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Dinitropyridines: Synthesis and Reactions

Starosotnikov,

Bastrakov

2024

Asian J Org Chem

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Dinitropyridines are one of the promising classes of heterocyclic compounds. They are considered as useful precursors of explosives and energetic compounds, agrochemicals, biosensors and biologically active compounds with diverse properties: antitumor, antiviral, anti‐neurodegenerative. Preliminary analysis of literature data shows that the chemistry of polynitropyridines has been actively developing over the past few decades. This is evidenced by the steadily growing annual number of publications. In this review the literature on the synthesis, reactions and practical application of isomeric dinitropyridines over a period of 2010‐2024 is analyzed.

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Nitropyridines 11. *Recyclization of quaternary nitropyridinium salts into substituted nitroanilines

Cited by 7 publications

References 16 publications

[6]–[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy

[6]–[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy

C₆‐Selective Direct Arylation of 2‐Phenylpyridine via an Activated N‐methylpyridinium Salt: A Combined Experimental and Theoretical Study

Dinitropyridines: Synthesis and Reactions

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Nitropyridines 11. *Recyclization of quaternary nitropyridinium salts into substituted nitroanilines

Cited by 7 publications

References 16 publications

[6]–[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy

[6]–[9]Metacyclophanes: Synthesis, Crystal Structures, and NMR and UV Spectroscopy

C6‐Selective Direct Arylation of 2‐Phenylpyridine via an Activated N‐methylpyridinium Salt: A Combined Experimental and Theoretical Study

Dinitropyridines: Synthesis and Reactions

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Product

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C₆‐Selective Direct Arylation of 2‐Phenylpyridine via an Activated N‐methylpyridinium Salt: A Combined Experimental and Theoretical Study