Photochemical transformations. Part 11. Photorearrangement of 1-(2-pyridyl)- and 1-(3-pyridyl)-2-nitropropenes

Hunt, R.; Reid, S. T.

doi:10.1039/p19770002462

Cited by 9 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1. The structure of (2a) was postulated by analogy to the photorearrangement of several a$-unsaturated nitroalkanes (Chapman et al, 1966; Hunt andReid, 1972, 1977), while that of (3a) derived from the observed oxadiazole formation (Clapp, 1976). Pfoertner and Daly (1987) recently confirmed the formation of 5-methyl-1,2,4-oxadiazole-3-carboxamides as the ultimate product of the photochemical rearrangement of 2-methyl-5-nitroimidazoles but failed to isolate the iminoketone intermediate in a state sufficiently pure to enable adequate spectral data to be obtained.…”

Section: Introductionmentioning

confidence: 99%

Photolytic Rearrangement of Metronidazole to 1‐hydroxyethyl‐2‐methyl‐4‐hydroxyimino‐5‐oxo‐imidazole and the Formation of Copper Complexes of These Compounds

Wilkins¹,

Moore

1988

Photochem & Photobiology

View full text Add to dashboard Cite

A labile intermediate in the photolytic rearrangement of the antibacterial drug, metronidazole, was identified by isolating the product of photolysis of metronidazole benzoate in methanol. The intermediate, 1-hydroxyethyl-2-methyl-4-hydroxyimino-5-oxo-imidazole, was shown to act as a bidentate chelating agent for copper(I1) ions, whereas metronidazole forms a weak monodentate complex. The intermediate may be relevant to the bioactivation mechanism of metronidazole.

show abstract

Section: Introductionmentioning

confidence: 99%

Photolytic Rearrangement of Metronidazole to 1‐hydroxyethyl‐2‐methyl‐4‐hydroxyimino‐5‐oxo‐imidazole and the Formation of Copper Complexes of These Compounds

Wilkins¹,

Moore

1988

Photochem & Photobiology

View full text Add to dashboard Cite

show abstract

“…This material could be prepared in a manner similar to 1 . A previous report described a two-step photochemical route which afforded oxime 6 in 12% yield . We prepare this same species in 65% yield from pyrid-2-yl acetone 7 by treatment with sodium nitrite in sulfuric acid.…”

mentioning

confidence: 99%

[1,10]-Phenanthrolin-2-yl Ketones and Their Coordination Chemistry

Bark

Thummel

2005

Inorg. Chem.

View full text Add to dashboard Cite

A synthetic protocol involving the Friedländer reaction of 8-amino-7-quinolinecarbaldehyde followed by potassium dichromate oxidation was applied to 2,3,4-pentanetrione-3-oxime and 1-(pyrid-2'-yl)propane-1,2-dione-1-oxime to provide the ligands di-(phenathrolin-2-yl)-methanone (1) and phenanthrolin-2-yl-pyrid-2-yl-methanone (8), respectively. Ligand 1 complexed as a planar tetradentate with Pd(II) to form [Pd(1)](BF4)2 and with Ru(II) and two 4-substituted pyridines (4-R-py) to form [Ru(1)(4-R-py)2](PF6)2 where R = CF3, CH3, and Me2N. With [Ru(bpy)2Cl2], the dinuclear complex [(bpy)2Ru(1)Ru(bpy)2](PF6)4 was formed (bpy = 2,2'-bipyridine). Ligand 8 afforded the homoleptic Ru(II) complex [Ru(8)2](PF6)2, as well as the heteroleptic complex [Ru(8)(tpy)](PF6)2 (tpy = 2,2';6,2''-terpyridine). The ligands and complexes were characterized by their NMR and IR spectra, as well as an X-ray structure determination of [Ru(1)(4-CH3-py)2](PF6)2. Electrochemical analysis indicated metal-based oxidation and ligand-based reduction that was consistent with results from electronic absorption spectra. The complexes [Ru(1)(4-R-py)2](PF6)2 were sensitive to the 4-substituent on the axial pyridine: electron donor groups facilitated the oxidation while electron-withdrawing groups impeded it.

show abstract

ChemInform Abstract: PHOTOCHEMICAL TRANSFORMATIONS. PART 11. PHOTOREARRANGEMENT OF 1‐(2‐PYRIDYL)‐ AND 1‐(3‐PYRIDYL)‐2‐NITROPROPENES

Hunt¹,

Reid²

1978

Chemischer Informationsdienst

View full text Add to dashboard Cite

show abstract

Photochemical transformations. Part 11. Photorearrangement of 1-(2-pyridyl)- and 1-(3-pyridyl)-2-nitropropenes

Abstract: bury, Kent CT2 7NHPyrex-filtered irradiation of 1 -(2-pyridy1)-and 1 -(3-pyridyl)-2-nitropropene in acetone solution gives 1 -(2-pyridyl)and 1 -(3-pyridyl) -1 -hydroxyiminopropan-2-one, respectively, in high yield.

Cited by 9 publications

References 0 publications

Photolytic Rearrangement of Metronidazole to 1‐hydroxyethyl‐2‐methyl‐4‐hydroxyimino‐5‐oxo‐imidazole and the Formation of Copper Complexes of These Compounds

Photolytic Rearrangement of Metronidazole to 1‐hydroxyethyl‐2‐methyl‐4‐hydroxyimino‐5‐oxo‐imidazole and the Formation of Copper Complexes of These Compounds

[1,10]-Phenanthrolin-2-yl Ketones and Their Coordination Chemistry

ChemInform Abstract: PHOTOCHEMICAL TRANSFORMATIONS. PART 11. PHOTOREARRANGEMENT OF 1‐(2‐PYRIDYL)‐ AND 1‐(3‐PYRIDYL)‐2‐NITROPROPENES

Contact Info

Product

Resources

About