Copper-catalyzed oxygenation of 3-hydroxy-2-phenylquinolin-4(1H)-one: Synthesis, structure and spectral properties of [Cu(idpa)(N-baa)]ClO 4, [idpa = 3,3′-iminobis(N,N-dimethylpropylamine), N-baaH = N-benzoylanthranilic acid]

J. Kaizer, Tamás Csay, Miklós Czaun, G. Speier, Marius Réglier, Michel Giorgi

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Reaction of one molar equivalent of 3,3′-iminobis(N,N- dimethylpropylamine (idpa)), N-benzoylanthranilic acid (N-baaH) and [Cu(CH 3CN)4](ClO4) in acetonitrile resulted in the formation of a stable ionic copper(II) complex without additional solvent coordination. The composition and molecular structure of [Cu(idpa)(N-baa)] ClO4 was fully determined by IR, UV-vis, and X-ray crystal analysis. The complex has a distorted square planar CuN3O core. The oxygenation of 3-hydroxy-2-phenylquinolin-4(1H)-one (QuinH2) using [Cu(idpa)(N-baa)]ClO4 as a catalyst results in the oxidative cleavage of the heterocyclic ring to give a N-benzoylanthranilic acid and CO as a mimic of quercetinase and 3-hydroxy-1,4-dihydroquinolin-4-one 2,4-dioxygenase action.

Original languageEnglish
Pages (from-to)813-816
Number of pages4
JournalInorganic Chemistry Communications
Volume8
Issue number9
DOIs
Publication statusPublished - Sep 2005

Fingerprint

Oxygenation
oxygenation
Copper
quercetin 2,3-dioxygenase
copper
acids
Acids
synthesis
Acetonitrile
Molecular structure
acetonitrile
Dioxygenases
cleavage
molecular structure
methylidyne
Carbon Monoxide
Molecular Structure
catalysts
X rays
Crystals

Keywords

  • 3-Hydroxy-2-phenylquinolin-4(1H)-one
  • Copper
  • Dioxygenation
  • N-benzoylanthranilic acid
  • Quercetinase

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

@article{79a120b03ac24044aa0c63a2993c5b9a,
title = "Copper-catalyzed oxygenation of 3-hydroxy-2-phenylquinolin-4(1H)-one: Synthesis, structure and spectral properties of [Cu(idpa)(N-baa)]ClO 4, [idpa = 3,3′-iminobis(N,N-dimethylpropylamine), N-baaH = N-benzoylanthranilic acid]",
abstract = "Reaction of one molar equivalent of 3,3′-iminobis(N,N- dimethylpropylamine (idpa)), N-benzoylanthranilic acid (N-baaH) and [Cu(CH 3CN)4](ClO4) in acetonitrile resulted in the formation of a stable ionic copper(II) complex without additional solvent coordination. The composition and molecular structure of [Cu(idpa)(N-baa)] ClO4 was fully determined by IR, UV-vis, and X-ray crystal analysis. The complex has a distorted square planar CuN3O core. The oxygenation of 3-hydroxy-2-phenylquinolin-4(1H)-one (QuinH2) using [Cu(idpa)(N-baa)]ClO4 as a catalyst results in the oxidative cleavage of the heterocyclic ring to give a N-benzoylanthranilic acid and CO as a mimic of quercetinase and 3-hydroxy-1,4-dihydroquinolin-4-one 2,4-dioxygenase action.",
keywords = "3-Hydroxy-2-phenylquinolin-4(1H)-one, Copper, Dioxygenation, N-benzoylanthranilic acid, Quercetinase",
author = "J. Kaizer and Tam{\'a}s Csay and Mikl{\'o}s Czaun and G. Speier and Marius R{\'e}glier and Michel Giorgi",
year = "2005",
month = "9",
doi = "10.1016/j.inoche.2005.06.007",
language = "English",
volume = "8",
pages = "813--816",
journal = "Inorganic Chemistry Communication",
issn = "1387-7003",
publisher = "Elsevier BV",
number = "9",

}

TY - JOUR

T1 - Copper-catalyzed oxygenation of 3-hydroxy-2-phenylquinolin-4(1H)-one

T2 - Synthesis, structure and spectral properties of [Cu(idpa)(N-baa)]ClO 4, [idpa = 3,3′-iminobis(N,N-dimethylpropylamine), N-baaH = N-benzoylanthranilic acid]

AU - Kaizer, J.

AU - Csay, Tamás

AU - Czaun, Miklós

AU - Speier, G.

AU - Réglier, Marius

AU - Giorgi, Michel

PY - 2005/9

Y1 - 2005/9

N2 - Reaction of one molar equivalent of 3,3′-iminobis(N,N- dimethylpropylamine (idpa)), N-benzoylanthranilic acid (N-baaH) and [Cu(CH 3CN)4](ClO4) in acetonitrile resulted in the formation of a stable ionic copper(II) complex without additional solvent coordination. The composition and molecular structure of [Cu(idpa)(N-baa)] ClO4 was fully determined by IR, UV-vis, and X-ray crystal analysis. The complex has a distorted square planar CuN3O core. The oxygenation of 3-hydroxy-2-phenylquinolin-4(1H)-one (QuinH2) using [Cu(idpa)(N-baa)]ClO4 as a catalyst results in the oxidative cleavage of the heterocyclic ring to give a N-benzoylanthranilic acid and CO as a mimic of quercetinase and 3-hydroxy-1,4-dihydroquinolin-4-one 2,4-dioxygenase action.

AB - Reaction of one molar equivalent of 3,3′-iminobis(N,N- dimethylpropylamine (idpa)), N-benzoylanthranilic acid (N-baaH) and [Cu(CH 3CN)4](ClO4) in acetonitrile resulted in the formation of a stable ionic copper(II) complex without additional solvent coordination. The composition and molecular structure of [Cu(idpa)(N-baa)] ClO4 was fully determined by IR, UV-vis, and X-ray crystal analysis. The complex has a distorted square planar CuN3O core. The oxygenation of 3-hydroxy-2-phenylquinolin-4(1H)-one (QuinH2) using [Cu(idpa)(N-baa)]ClO4 as a catalyst results in the oxidative cleavage of the heterocyclic ring to give a N-benzoylanthranilic acid and CO as a mimic of quercetinase and 3-hydroxy-1,4-dihydroquinolin-4-one 2,4-dioxygenase action.

KW - 3-Hydroxy-2-phenylquinolin-4(1H)-one

KW - Copper

KW - Dioxygenation

KW - N-benzoylanthranilic acid

KW - Quercetinase

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