Reaction of 1,3,5-Trinitrobenzene with Phenols: Synthesis of 3,5-Dinitrophenyl Aryl Ethers

Шевелев, С. А.; Дутов, М. Д.; Вацадзе, И. А.; Serushkina, O. V.; Rusanov, A. L.; Andrievskii, Aleksandr M.

doi:10.1070/mc1995v005n04abeh000505

Cited by 24 publications

(13 citation statements)

References 8 publications

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“…As mentioned above, quinolines 1 and 2 do not undergo a reaction with phenol in the presence of a base. At the same time, the nitro group of 1,3,5‐trinitrobenzene smoothly underwent a substitution reaction with the PhO − group in aprotic dipolar solvents [DMF, N ‐methylpyrrolidone (NMP)] at 80 °C …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

et al. 2016

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An efficient method was developed for the synthesis of 5,7-dinitroquinoline and its N-oxide. The reactions of these compounds with either thiols or sodium azide resulted in the regiospecific substitution of 5-NO 2 group and the formation of previously unknown quinoline derivatives.The 5-azido derivatives underwentr eactions with 1,3-dicarbonyl compounds and, depending on the nature of reagent, afforded either 5-(1,2,3-triazol)-1-yl-or 5-amino-7-nitroquinolines, which have been previously inaccessible by using other methods.Scheme1.Synthesis of 5,7-dinitroquinolines 1 and 2 (DMF = N,N-dimethylformamide). [a] Dr.A .M.S tarosotnikov,V .V .Nikol'skiy,A.N.B orodulya, Dr.Scheme2.Reactions of 5,7-dinitroquinolines with O-and N-nucleophiles. Scheme3.Reactions of 5,7-dinitroquinolines with thiols. Scheme4.Nucleophilic aromatic substitution of the nitro group(Nu = nuclophile).

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Section: Resultsmentioning

confidence: 99%

Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

et al. 2016

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“…3,5-Dinitrodiphenyl ether and 3,5-dinitrodiphenyl sulfide were prepared and purified in accordance with previously described methods [7,8].…”

Section: Synthesis Of the Monomersmentioning

confidence: 99%

“…Oxidative demethylation of TNT leading to the formation of TNB was carried out in accordance with previously published methods [6] (scheme 1). The nitro groups in TNB were partially replaced for phenoxy and phenylthio groupings [7,8] using aromatic nucleophilic nitrodisplacement reactions [9] (scheme 2).…”

Section: Synthesis and Characterization Of The Sulfonated Monomersmentioning

confidence: 99%

New Sulfonated Polyethers and Polynaphthylimides based on TNT Derivatives

Русанов

Komarova

Булычева

et al. 2009

High Performance Polymers

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New sulfonated and non-sulfonated monomers — dinitro and diamino compounds — were prepared on the basis of 1,3,5-trinitrobenzene (TNB) which is the demethylation product of 2,4,6-trinitrotoluene (TNT). The sulfonated dinitrocompounds interacted with different binuclear bis-phenols under the conditions of aromatic nucleophilic nitrodisplacement reactions. Polyethers of moderate molecular weights were prepared on the basis of dinitrocompound containing electron-withdrawing 3,5-dinitrodiphenyl sulfone-4′-sulfonic acid “bridging” groups. Copolymers and blends with other sulfonated polymers were prepared to improve the film-forming properties of the polyethers developed on the basis of 3,5-dinitrodiphenyl sulfone-4′-sulfonic acid. High molecular weight sulfonated polynaphthylimides were prepared by the interaction of sulfonated diamine containing electron-donating ether group — 3,5-diaminodiphenyl ether-4′-sulfonic acid — with bis(naphthalic anhydride)s. The sulfonated polyethers and polynaphthylimides thus obtained contain sulfonic acid groups in the side chains.

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“…The synthesis began with construction of the appropriately substituted nitroaniline as shown in Scheme 1. Trinitrobenzene was carefully reacted with appropriately substituted phenols according to the general method of Shevelev et al 18 to provide the corresponding dinitrophenoxy compounds 2 a–j , and k. The dinitro intermediates were then partially reduced to the corresponding nitroanilines ( 3 a–j, and k ) using ammonium sulfide. These nitroanilines were condensed with the chloroquinazoline compound 4 19 to provide the corresponding substituted 4-aminoquinazolines 1 a–j and k .…”

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Discovery of substituted 4-aminoquinazolines as selective Toll-like receptor 4 ligands

Nour

Hayashi

Chan

et al. 2014

Bioorganic & Medicinal Chemistry Letters

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The Toll-like receptors (TLRs) are critical components of the innate immune system that regulate immune recognition in part through NF-κB activation. A human cell-based high throughput screen (HTS) revealed substituted 4-aminoquinazolines to be small molecular weight activators of NF-κB. The most potent hit compound predominantly stimulated through the human TLR4/MD2 complex, and had less activity with the mouse TLR4/MD2. There was no activity with other TLRs and the TLR4 activation was MD-2 dependent and CD14 independent. Synthetic modifications of the quinazoline scaffold at the 2 and 4 positions revealed trends in structure-activity relationships with respect to TLR dependent production of the NF-κB associated cytokine IL-8 in human peripheral blood mononuclear cells, as well as IL-6 in mouse antigen presenting cells. Furthermore, the hit compound in this series also activated the interferon signaling pathway resulting in type I interferon production. Substitution at the O-phenyl moiety with groups such as bromine, chlorine and methyl resulted in enhanced immunological activity. Computational studies indicated that the 4-aminoquinazoline compounds bind primarily to human MD-2 in the TLR4/MD-2 complex. These small molecules, which preferentially stimulate human rather than mouse innate immune cells, may be useful as adjuvants or immunotherapeutic agents.

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Reaction of 1,3,5-Trinitrobenzene with Phenols: Synthesis of 3,5-Dinitrophenyl Aryl Ethers

Cited by 24 publications

References 8 publications

Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

New Sulfonated Polyethers and Polynaphthylimides based on TNT Derivatives

Discovery of substituted 4-aminoquinazolines as selective Toll-like receptor 4 ligands

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