p-Nitrosophenol chemistry. II. Amination of p-nitrosophenol ethers with primary aromatic amines

Hays, John T.; Young, Herbert Lewis; Espy, Herbert H.

doi:10.1021/jo01277a039

Cited by 12 publications

(16 citation statements)

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“…Cl H (28) tb It is to be noted that the infrared spectrum of the crude product is different from that of the recrystallized product; however, the properties of the latter are in agreement with that reported in the earlier literature. [71] In a well-ventilated hood, to a stirred solution of 4.7 gm (0.08 mole) of norbornene and 7.02 gm (0.06 mole) of isopentyl nitrite in 10 ml of ethanol, cooled to 0°C in an ice-salt bath, is added dropwise, over a \ hr period, a solu tion of 10 gm (0.59 mole) of 48 % hydrobromic acid in 12 ml of ethanol.…”

Section: No Hsupporting

confidence: 88%

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C-Nitroso Compounds

1971

Organic Chemistry: A Series of Monographs

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Section: No Hsupporting

confidence: 88%

“…(Eq. J-NH 2 CÎ^COTH^ HO-L T J-NH 2 Amination of />-nitrosophenol ethers with primary aromatic amines[28] (Eq. .HN II (CH 3 ) 2 N-JL T J-NHCH 2 CH 2 OH CH 3 CO 2 H NaN0 2 o Η Ν^γ Ν Ο (CH 3 ) 2 N-i^ J-NHCH 2 CH 2 OHHO A .…”

mentioning

confidence: 99%

C-Nitroso Compounds

1971

Organic Chemistry: A Series of Monographs

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“…(1). The compound was prepared by etherification of p-nitrosophenol (Hays et al 1967a). Green crystals, m.p.…”

Section: Methodsmentioning

confidence: 99%

“…A third secondary product, 4-ethoxy-4'-nitrosodiphenylamine (2), was identified during incubation of 4-ethoxynitrosobenzene (1) with human erythrocytes (Klehr et al 1987). These latter compounds are conceivably formed through a condensation reaction between the parent amine or the hydroxylamine and 1 (Wirth et al 1980;Hays et al 1967b). Both the azo-and azoxycompounds as well as 4-ethoxyaniline and 4ethoxynitrobenzene are non-mutagenic in the absence of metabolically activating systems (Wirth et al 1982).…”

Section: -Ethoxyaniline (P-phenetidine)mentioning

confidence: 99%

Cellular Effects of Some Metabolic Oxidation Products Pertinent to 4‐Ethoxyaniline

Lindqvist

Moldéus

Lindeke³

1991

Pharmacology & Toxicology

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The toxicity of some metabolic products pertinent to 4-ethoxyaniline in isolated hepatocytes were investigated. The compounds investigated were 4-ethoxynitrosobenzene (1), 4-ethoxy-4'-nitrosodiphenylamine (2), 3,6-bis(4-ethoxy-phenylimino)-4-ethoxy-1,4-cyclohexadienylamine (3), 4-(4-ethoxyphenylimino)-2,3-dimethyl-2,5-cyclohexadiene-1-one (4) and 4-(4-ethoxyphenylimino)-2,6-dimethyl-2,5-cyclohexadiene-1-one (5). Of these, 1, 2 and 3 are oxidation products of 4-ethoxyaniline. Compounds 4 and 5 are dimethyl analogues of previously investigated oxidation product 4-(4-ethoxyphenylimino(-2,5-cyclohexadiene-1-one (NEPBQI). Among the investigated compounds, 1 and 2 were the most toxic towards isolated hepatocytes. In hepatocytes treated with compounds 1, 2 and 4, loss of cell viability was also accompanied by surface bleb formation. All compounds except 3 reacted with GSH resulting in depletion of cellular GSH. No formation of GSSG was observed, however. Thus, the GSH depletion was apparently due to conjugate formation rather than oxidation. No superoxide dismutase inhibitable reduction of acetylated cytochrome c was observed, thus none of the compounds undergoes measurable redox cycling.

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“…25 nitro-substituted compounds 7 from the parent nitroso precursors 3 and the aniline 1 by nucleophilic aromatic substitution seems to be a less reasonable mechanism under the strong oxidizing reaction conditions employed. 28 The formation of 8 is expected to proceed by a reaction sequence involving an initial oxidative head-to-ortho coupling step. 25,27 In summary, we have shown that the oxidation of anilines 1 with 30% H 2 O 2 , catalyzed by selenium dioxide in methanol at room temperature, provides a simple and efficient method for the preparation of a variety of azoxyarenes 6.…”

mentioning

confidence: 99%

Oxidation of Anilines with Hydrogen Peroxide and Selenium Dioxide as Catalyst

Gebhardt¹,

Priewisch²,

Irran³

et al. 2008

Synthesis

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A variety of substituted anilines are selectively oxidized to afford high yields of azoxyarenes by using 30% hydrogen peroxide and selenium dioxide as catalyst in methanol at room temperature. The oxidation of 4-alkoxyanilines under the same reaction conditions furnishes the corresponding 4-alkoxy-N-(4-nitrophenyl)anilines in reasonable yields, alongside other oxidation byproducts. The structure of 4-methoxy-N-(4-nitrophenyl)aniline is elucidated by X-ray crystal structure analysis. From these results, some general aspects of the reaction pathways of aniline oxidation are discussed.

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p-Nitrosophenol chemistry. II. Amination of p-nitrosophenol ethers with primary aromatic amines

Cited by 12 publications

References 0 publications

C-Nitroso Compounds

C-Nitroso Compounds

Cellular Effects of Some Metabolic Oxidation Products Pertinent to 4‐Ethoxyaniline

Oxidation of Anilines with Hydrogen Peroxide and Selenium Dioxide as Catalyst

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p-Nitrosophenol chemistry. II. Amination of p-nitrosophenol ethers with primary aromatic amines

Cited by 12 publications

References 0 publications

C-Nitroso Compounds

C-Nitroso Compounds

Cellular Effects of Some Metabolic Oxidation Products Pertinent to 4‐Ethoxyaniline

Oxidation of Anilines with Hydrogen Peroxide and Selenium Dioxide as ­Catalyst

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Product

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Oxidation of Anilines with Hydrogen Peroxide and Selenium Dioxide as Catalyst