Synthesis of functionalized 4-nitroanilines by ring transformation of dinitropyridone with enaminones

Naito, Saki; Yokoyama, Saichiro; Asahara, Haruyasu; Nishiwaki, Nagatoshi

doi:10.1016/j.tetlet.2017.11.003

Cited by 5 publications

(1 citation statement)

References 16 publications

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“…For this purpose, relatively stable enaminones 47 prepared from 1,3-dicarbonyl compounds 7 and amine 45 are considered suitable. When dinitropyridone 1 reacts with enaminone 47 , nucleophilic-type ring transformation proceeds to afford 2-functionalized 4-nitroaniline 48 ( Table 11 ) [ 58 ]. This protocol facilitates the modification of the functional group and amino group of 48 by altering 1,3-dicarbonyl compounds 7 and amine 45 .…”

Section: Three-component Ring Transformation (Tcrt)mentioning

confidence: 99%

Synthesis of Nitroaromatic Compounds via Three-Component Ring Transformations

Asahara

Nishiwaki

2021

Molecules

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1-Methyl-3,5-dinitro-2-pyridone serves as an excellent substrate for nucleophilic-type ring transformation because of the electron deficiency and presence of a good leaving group. In this review, we focus on the three-component ring transformation (TCRT) of dinitropyridone involving a ketone and a nitrogen source. When dinitropyridone is allowed to react with a ketone in the presence of ammonia, TCRT proceeds to afford nitropyridines that are not easily produced by alternative procedures. Ammonium acetate can be used as a nitrogen source instead of ammonia to undergo the TCRT, leading to nitroanilines in addition to nitropyridines. In these reactions, dinitropyridone serves as a safe synthetic equivalent of unstable nitromalonaldehyde.

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Section: Three-component Ring Transformation (Tcrt)mentioning

confidence: 99%

Synthesis of Nitroaromatic Compounds via Three-Component Ring Transformations

Asahara

Nishiwaki

2021

Molecules

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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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