Synthesis of substituted anthranils by deoxidation of o-nitrosoacetylbenzenes

Shabarov, Yu. S.; Mochalov, S. S.; Федотов, А. Н.; Kalashnikov, V. V.

doi:10.1007/bf00471290

Cited by 3 publications

(2 citation statements)

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Section: Resultsmentioning

confidence: 93%

“…This peak was present in chromatograms run immediately after mixing 2-nitrosoacetophenone with DTT and evidently corresponds to the equilibrium mixture of 7 and 8. Reduction of 2-nitrosoacetophenone to 3-methylanthranil has previously been reported by electrochemistry under acidic conditions, 21 with triphenylphosphine 22 and with bisulfite. 23 Nevertheless, on the time scale of most biological experiments that use caged compounds, the major byproduct species present must be the tautomeric forms 7 and 8 of 2-hydroxylaminoacetophenone, although when a monofunctional thiol is used significant concentrations of the initial thiol adduct with 2-nitrosoacetophenone may also be present.…”

Section: Resultsmentioning

confidence: 94%

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Time-Resolved Infrared Spectroscopy of Intermediates and Products from Photolysis of 1-(2-Nitrophenyl)ethyl Phosphates: Reaction of the 2-Nitrosoacetophenone Byproduct with Thiols

Barth¹,

Corrie²,

Gradwell³

et al. 1997

J. Am. Chem. Soc.

117

114

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Rapid scan Fourier transform infrared (FTIR) spectroscopy and time-resolved single wavelength infrared (IR) spectroscopy have been applied to study the mechanism of photochemical release of adenosine 5‘-triphosphate (ATP) from its P 3-[1-(2-nitrophenyl)ethyl] ester (caged ATP). Bands arising from phosphate and non-phosphate vibrations characteristic of the aci-nitro anion intermediate and from free ATP and byproducts of the nitrophenylethyl group have been assigned using 13C, 15N, and 18O isotopomers of caged ATP. Monitoring several of these bands using time-resolved single frequency IR spectroscopy confirms that release of ATP occurs in a single exponential process synchronous with the decay of the aci-nitro anion intermediate. Spectral characteristics of the reaction products arising from the 1-(2-nitrophenyl)ethyl group in the absence and presence of dithiothreitol (DTT) have been determined. The major final byproduct from photolysis conducted in the presence of DTT is 3-methylanthranil. The mechanism of formation of this compound from 2-nitrosoacetophenone has been investigated in detail by a combination of spectroscopic, kinetic, and chemical methods and reconciled with earlier data. The byproduct species likely to be present on the time scale of most biological experiments using caged compounds is 2-hydroxylaminoacetophenone as a mixture of ring-chain tautomers.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 94%