The Preparation of β-Keto Amines by the Mannich Reaction

Blicke, F. F.; Burckhalter, J. H.

doi:10.1021/ja01254a059

Cited by 54 publications

(12 citation statements)

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“…[56] 1-(2-(3'-Isoquinolinyl)-2-oxoethyl)pyridinium iodide was prepared by heating 3-acetylisoqulinoline with excess I 2 in pyridine for 2 h. [57][58][59] 3-Dimethylamino-1-(2'-naphthyl)propanone hydrochloride salt was synthesized by refluxing 2-acetylnaphthalene, paraformaldehyde and dimethylamine hydrochloride in the presence of conc. HCl in 95 % ethanol for 24 h. [59] The a,b-unsaturated ketones were prepared according to literature methods. [60,61] The (RC^N^NH) ligands a-f were prepared by modification of published procedures.…”

Section: Methodsmentioning

confidence: 99%

Platinum(II) Complexes with π‐Conjugated, Naphthyl‐Substituted, Cyclometalated Ligands (RC^N^N): Structures and Photo‐ and Electroluminescence

Kui

Sham

Cheung

et al. 2006

Chemistry A European J

161

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The crystal structures and photophysical properties of mononuclear [(RC N N)PtX](ClO4)n ((RC N N)=3-(6'-(2''-naphthyl)-2'-pyridyl)isoquinolinyl and derivatives; X=Cl, n=0; X=PPh(3) or PCy(3), n=1), dinuclear [(RC N N)2Pt2(mu-dppm)](ClO4)2 (dppm=bis(diphenyphosphino)methyl) and trinuclear [(RC N N)3Pt3(mu-dpmp)](ClO4)3 (dpmp=bis(diphenylphosphinomethyl)phenylphosphine) complexes are presented. The crystal structures show extensive intra- and/or intermolecular pipi interactions; the two (RC N N) planes of [(RC N N)2Pt2(mu-dppm)](ClO4)2 (R=Ph, 3,5-tBu2Ph or 3,5-(CF3)2Ph) are in a nearly eclipsed configuration with torsion angles close to 0 degrees. [(RC N N)PtCl], [(RC N N)2Pt2(mu-dppm)](ClO4)2, and [(RC N N)3Pt3(mu-dpmp)](ClO4)3 are strongly emissive with quantum yields of up to 0.68 in CH2Cl2 or MeCN solution at room temperature. The [(RC N N)PtCl] complexes have a high thermal stability (T(d)=470-549 degrees C). High-performance light-emitting devices containing [(RC N N)PtCl] (R=H or 3,5-tBu2Ph) as a light-emitting material have been fabricated; they have a maximum luminance of 63,000 cd m(-2) and CIE 1931 coordinates at x=0.36, y=0.54.

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Section: Methodsmentioning

confidence: 99%

Platinum(II) Complexes with π‐Conjugated, Naphthyl‐Substituted, Cyclometalated Ligands (RC^N^N): Structures and Photo‐ and Electroluminescence

Kui

Sham

Cheung

et al. 2006

Chemistry A European J

161

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“…A similar by-product has been previously reported. [23] The product was purified by washing with acetone and recrystallization from acetone/ethanol to give a colourless powder. The acetone washings were worked up to obtain the dimer.…”

Section: Resultsmentioning

confidence: 99%

The syntheses, characterization and in vitro metabolism of nitracaine, methoxypiperamide and mephtetramine

Power

Scott

Gardner

et al. 2014

Drug Testing and Analysis

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Three legal highs; nitracaine (3-(diethylamino)-2,2-dimethylpropyl 4-nitrobenzoate), methoxypiperamide (MEOP, (4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone) and mephtetramine (MTTA, 2-((methylamino)methyl)-3,4-dihydronaphthalen-1(2H)-one) appeared in 2013 as new psychoactive substances (NPS) on Internet websites selling 'research chemicals'. These compounds were synthesized and analyzed via our synthesize, analyze, and metabolize (SAM) protocol. Nitracaine was synthesized by the transesterification of methyl 4-nitrobenzoate with 3-(diethylamino)-2,2-dimethylpropan-1-ol. Methoxypiperamide was synthesized by the reaction of 4-methoxybenzoyl chloride with 1-methylpiperazine, and mephtetramine through the Mannich reaction of 1-tetralone with paraformaldehyde and methylamine hydrochloride. Each compound was characterized by nuclear magnetic resonance (NMR), gas chromatography with electron impact mass spectrometry (GC-EIMS), liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS), and high resolution electrospray ionization mass spectrometry (HR-ESI-MS). A sample of nitracaine was also test-purchased from an Internet vendor and its structure confirmed by GC-EIMS and LC-ESI-MS. Finally, the in vitro metabolism of the nitracaine, mephtetramine, and methoxypiperamide was investigated, using a human microsomal liver extract, in order to tentatively identify potential metabolites that may be encountered in the analysis of biological samples in clinical or toxicology labs. The use of our SAM protocol highlights the ability of academic research labs to quickly respond to and disseminate information about emerging NPS.

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“…The name and the molecular structure of the three used β-aminoketone derivatives are as shown below: These compounds were prepared according to reported methods [15][16][17][18]. These compounds were subjected to recrystallisation using ethanol and identified by elemental analysis and IR spectra.…”

Section: Methodsmentioning

confidence: 99%

Some beta-Aminoketone Derivatives as Corrosion Inhibitors for Nickel in Hydrochloric Acid Solution

Elewady¹,

El-Askalany²,

Molouk³

2007

Port. Electrochim. Acta

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The use of some β-aminoketone derivatives as corrosion inhibitors for nickel in 2 M acid chloride solution was investigated by gravimetric and galvanostatic polarization techniques. It was found that the investigated compounds behave as inhibitors for nickel dissolution and their inhibition efficiencies increase by the addition of iodide ions. Also, the adsorption isotherms were studied and it was found to follow the Frumkin's adsorption isotherm. By increasing the temperature of the corrosive medium containing different concentrations of the tested inhibitors, the corrosion rate of nickel increases, indicating that these inhibitors are physically adsorbed on the metal surface. Finally, some quantum chemical quantities such as HOMO, LUMO and dipole moment of the inhibitors were calculated and correlated with the rate of corrosion.

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The Preparation of β-Keto Amines by the Mannich Reaction

Cited by 54 publications

References 0 publications

Platinum(II) Complexes with π‐Conjugated, Naphthyl‐Substituted, Cyclometalated Ligands (RC^N^N): Structures and Photo‐ and Electroluminescence

Platinum(II) Complexes with π‐Conjugated, Naphthyl‐Substituted, Cyclometalated Ligands (RC^N^N): Structures and Photo‐ and Electroluminescence

The syntheses, characterization and in vitro metabolism of nitracaine, methoxypiperamide and mephtetramine

Some beta-Aminoketone Derivatives as Corrosion Inhibitors for Nickel in Hydrochloric Acid Solution

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