2‐Nitro‐4‐Methoxyaniline

Fanta, Paul E.; Tarbell, D. S.

doi:10.1002/0471264180.os025.28

Cited by 3 publications

(3 citation statements)

References 5 publications

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“…Following the standard procedure in a gram‐scale, product 2 v was obtained in good yield after purification (Scheme ). We must highlight that aniline 1 v was prepared by nitration from p ‐anisidine (in three steps) following a reported procedure, the hydrodeamination of which also demonstrates the potential of this method to use the amino functionality as a traceless directing group in S E Ar.…”

Section: Resultsmentioning

confidence: 96%

Salicylic Acid‐Catalyzed One‐Pot Hydrodeamination of Aromatic Amines by tert‐Butyl Nitrite in Tetrahydrofuran

2017

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A significant acceleration in the hydrodeamination of in situ formed diazonium salts (from aromatic amines) has been observed in the presence of 10-mol% salicylic acid, using tetrahydrofuran as the hydrogen donor. The reaction proceeds efficiently at 20 8C for a wide range of substituted anilines, even at 10-mmol scale, without any other additive. The same protocol has been adapted to the selective deuterodeamination of some aromatic amines. Control experiments clearly show that aryl radicals are involved in the reaction mechanism.

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Section: Resultsmentioning

confidence: 96%

Salicylic Acid‐Catalyzed One‐Pot Hydrodeamination of Aromatic Amines by tert‐Butyl Nitrite in Tetrahydrofuran

2017

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“…In summary, 6-(4-aminophenoxy)hexanol ( 1 ) was synthesized using the reported method [32] . Nitration of 1 was achieved as described [33] and involved conversion of 1 to the acetamide followed by nitration with concentrated nitric acid to give 2. Deprotection then gave the nitroaniline 3 in 48% overall yield from 1.…”

Section: Methodsmentioning

confidence: 99%

A mitochondria-targeted mass spectrometry probe to detect glyoxals: implications for diabetes

Pun

Logan

Darley‐Usmar

et al. 2014

Free Radical Biology and Medicine

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The glycation of protein and nucleic acids that occurs as a consequence of hyperglycemia disrupts cell function and contributes to many pathologies, including those associated with diabetes and aging. Intracellular glycation occurs after the generation of the reactive 1,2-dicarbonyls methylglyoxal and glyoxal, and disruption of mitochondrial function is associated with hyperglycemia. However, the contribution of these reactive dicarbonyls to mitochondrial damage in pathology is unclear owing to uncertainties about their levels within mitochondria in cells and in vivo. To address this we have developed a mitochondria-targeted reagent (MitoG) designed to assess the levels of mitochondrial dicarbonyls within cells. MitoG comprises a lipophilic triphenylphosphonium cationic function, which directs the molecules to mitochondria within cells, and an o-phenylenediamine moiety that reacts with dicarbonyls to give distinctive and stable products. The extent of accumulation of these diagnostic heterocyclic products can be readily and sensitively quantified by liquid chromatography–tandem mass spectrometry, enabling changes to be determined. Using the MitoG-based analysis we assessed the formation of methylglyoxal and glyoxal in response to hyperglycemia in cells in culture and in the Akita mouse model of diabetes in vivo. These findings indicated that the levels of methylglyoxal and glyoxal within mitochondria increase during hyperglycemia both in cells and in vivo, suggesting that they can contribute to the pathological mitochondrial dysfunction that occurs in diabetes and aging.

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“…Poor yields in the deprotection of the acetamide were observed under basic conditions (50−66%) . However, refluxing 21 in concentrated HCl resulted in efficient removal of the amide, and 15 precipitated out of solution in high yield.…”

Section: Synthetic Routesmentioning

confidence: 99%

The Synthesis and Resolution of 2,2‘-, 4,4‘-, and 6,6‘-Substituted Chiral Biphenyl Derivatives for Application in the Preparation of Chiral Materials

Montoya-Pelaez

Lata

et al. 2006

J. Org. Chem.

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Various routes were examined for the synthesis of chiral biphenyl species that are substituted at the 2,2', 4,4' and 6,6' positions. Because the biaryl bond is tetrasubstituted, many coupling reactions were not suitable. The most reliable coupling reaction proved to be the Ullmann, which gave the desired product in 82% yield. The products were required as the starting point for the preparation of chiral materials using these as the monomer. For this reason, a route was required that produced large quantities of both enantiomers. The two enantiomers were resolved at the penultimate step by the use of chiral HPLC. A complicating feature proved to be the necessity to have a reactive group at the 4,4' positions, which would permit polymerization though this point. Ultimately, we employed an Ullmann coupling on a dibrominated arene, which occurred selectively at the more hindered bromine by virtue of the directing effect of an ortho ester substituent.

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2‐Nitro‐4‐Methoxyaniline

Abstract: 2‐Nitro‐4‐methoxyaniline intermediate: 2‐nitro‐4‐methoxyacetanilide product: 2‐Nitro‐4‐methoxyaniline

Cited by 3 publications

References 5 publications

Salicylic Acid‐Catalyzed One‐Pot Hydrodeamination of Aromatic Amines by tert‐Butyl Nitrite in Tetrahydrofuran

Salicylic Acid‐Catalyzed One‐Pot Hydrodeamination of Aromatic Amines by tert‐Butyl Nitrite in Tetrahydrofuran

A mitochondria-targeted mass spectrometry probe to detect glyoxals: implications for diabetes

The Synthesis and Resolution of 2,2‘-, 4,4‘-, and 6,6‘-Substituted Chiral Biphenyl Derivatives for Application in the Preparation of Chiral Materials

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