Benzofuroxans: their synthesis, properties, and biological activity

Chugunova, Elena; Газизов, А. С.; Бурилов, А. Р.; Yusupova, L. M.; Пудовик, М. А.; Sinyashin, Оleg G.

doi:10.1007/s11172-019-2503-6

Cited by 17 publications

(18 citation statements)

References 126 publications

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“…However, the main limiting factors for the synthesis of benzofuroxans from 2-nitroarylazides are the two-stage method and the explosiveness of the arylazides used during isolation. 15 Therefore, to obtain the key benzofuroxan, the one-stage method of oxidative cyclization of 2-nitroanilines was examined because it proceeds under mild conditions and does not require hazardous reagents. This method was found to be suitable for the preparation of aminobenzofuroxans.…”

Section: Resultsmentioning

confidence: 99%

“…Several methods can be successfully used for the synthesis of benzofuroxans. [12][13][14][15] Among them, the most effective include thermolysis of 2-nitroarylazides and oxidative cyclization of 2nitroanilines. However, the main limiting factors for the synthesis of benzofuroxans from 2-nitroarylazides are the twostage method and the explosiveness of the arylazides used during isolation.…”

Section: Synthesismentioning

confidence: 99%

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Synthesis of 7-amino-6-halogeno-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides: a way forward for targeting hypoxia and drug resistance of cancer cells

Buravchenko

Scherbakov²,

Dezhenkova

et al. 2021

RSC Adv.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Synthesis of 7-amino-6-halogeno-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides: a way forward for targeting hypoxia and drug resistance of cancer cells

Buravchenko

Scherbakov²,

Dezhenkova

et al. 2021

RSC Adv.

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“…Finally, the ion m/z =817 (22 %) in the spectrum could be assigned to furazano‐dihydrofurazane derivative ( 13 ; M + , C 48 H 34 N 8 O 2 Cu). It is possible as the ortho ‐amino‐/nitro‐substituted aromatic compounds may transform easily into furoxans [43] followed by losing of the O ‐atom (at higher reaction temperature presumably via an intermolecular process). A number examples of furoxans deoxygenation can be found in the literature [44] .…”

Section: Resultsmentioning

confidence: 99%

“…Probably, the reactivity of porphyrins containing substituents in β ‐positions is different as compared to reactivity of typical aromatic compounds, e. g . benzene or naphthalene derivatives [43] …”

Section: Resultsmentioning

confidence: 99%

Studies on Synthesis of Porphyrins – β‐Substituted with Multiple Nitrogen‐containing Groups

Rosa

Ostrowski

2022

ChemistrySelect

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The synthesis of porphyrins with up to four nitrogen substituents at the β‐positions is described. meso‐Tetraarylporphyrin chelates (CuII, ZnII) upon reaction with nitric acid (yellow fuming HNO3, d=1.52, diluted to 30–50 %) in chloroform, under argon, gave mainly dinitro‐derivatives with combined yields of up to 57 %. These intermediates in the reaction with N,N,N‐trimethylhydrazinium iodide (TMHI) in the presence of a base (potassium methoxide, potassium hydroxide) formed β,β‐diamino‐β,β‐dinitro‐porphyrinates via vicarious nucleophilic substitution (VNS). The obtained products were characterized using 1H NMR, UV‐Vis, MS, and HR‐MS methods. Some attempts of further transformations (diazotisation followed by subsequent reactions, cyclizations, oxidation) were undertaken. At every stage of this investigation a number of various by‐products were identified. This type of highly nitrogen‐substituted β,β‐diamino‐β,β‐dinitro‐porphyrinates, practically not accessible by other methods, are attractive starting materials for synthesis of potential anticancer PDT agents.

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“…Further studies on the polymerization of these molecules to obtain conjugated polymers are currently underway. At last, this work could also be of interest in the field of medicinal chemistry, as heteroaromatic moieties are associated with a wide range of pharmacological activities. − …”

Section: Discussionmentioning

confidence: 99%

Biosourced Vanillin-Based Building Blocks for Organic Electronic Materials

et al. 2021

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Forest biomass is viewed as a significant source of organic carbon and thus the ideal replacement of petroleum products. From the resources derived from biomass, lignocellulose is the most abundant biobased material on earth. One of the aromatic added value compounds obtained from the depolymerization of lignin is vanillin. Here, we report the preparation of new compounds having benzothiophene, indole, isatin, benzofuroxan, benzofurazan, benzothiadiazole, and phthalimide heteroaromatic ring structures. More precisely, our results show that vanillin can be used as a biosourced starting material for the preparation of a variety of aromatic dibrominated monomers. X-ray crystallography on single crystals was also performed to obtain meaningful information on their solid-state ordering. This work opens the way to new, sustainable, biosourced aromatic materials (small molecules or polymers) for organic electronics.

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Benzofuroxans: their synthesis, properties, and biological activity

Cited by 17 publications

References 126 publications

Synthesis of 7-amino-6-halogeno-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides: a way forward for targeting hypoxia and drug resistance of cancer cells

Synthesis of 7-amino-6-halogeno-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides: a way forward for targeting hypoxia and drug resistance of cancer cells

Studies on Synthesis of Porphyrins – β‐Substituted with Multiple Nitrogen‐containing Groups

Biosourced Vanillin-Based Building Blocks for Organic Electronic Materials

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