A new synthesis of 3-phenoxazin-3-ones

Bird, C. W.; Latif, Marwa Abdel

doi:10.1016/0040-4020(80)80030-5

Cited by 19 publications

(1 citation statement)

References 11 publications

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“…21 Reaction with p-dinitrobenzene (Sigma-Aldrich) or o, p-dinitrobenzene chloride (Fluka AG, Buchs, Switzerland) in the presence of potassium carbonate (Merck, Darmstadt, Germany) in acetone produced the corresponding alkyl 3-hydroxy-5-(4'-nitrophenoxy) benzoates or alkyl 3-hydroxy-5-(2', 4'-dinitrophenoxy) benzoates, respectively. 22 A full interpretation of the 1 H and 13 C NMR shifts and coupling constants of spectra recorded on a Varian Fourier transform NMR spectrometer (Palo Alto, CA, USA) at 500 and 125 MHz revealed that the target compounds had been successfully synthesised in total yields of 27-54%.…”

Section: Methodsmentioning

confidence: 99%

Effect of nitro groups and alkyl chain length on the negative ion tandem mass spectra of alkyl 3-hydroxy-5-(4′-Nitrophenoxy) and alkyl 3-hydroxy-5-(2′, 4′-dinitrophenoxy) benzoates

Kangas

Franzén

Tois

et al. 1999

Rapid Commun. Mass Spectrom.

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Tandem mass spectrometric behaviour was studied for a small combinatorial library of alkyl 3-hydroxy-5-(4'-nitrophenoxy) benzoates (A1-A5) and alkyl 3-hydroxy-5-(2', 4'-dinitrophenoxy) benzoates (B1-B5). The spectra were recorded by negative ion electrospray low-energy collision induced dissociation (CID) tandem mass spectrometry. The product ion spectra of [M - H](-) of the benzoates A1-A5 are similar, as are those of benzoates B1-B5. However, the spectra of the B series compounds differ significantly from those of the A series owing to the second electron-withdrawing nitro substituent in the B compounds. In addition, the length of the alkyl chain has an effect on the fragmentation. However, both series of compounds exhibit an abundant nitrophenoxy ion formed by the loss of 3-hydroxybenzoate. This is at m/z 138 in A1-A5 and at m/z 183 in B1-B5. A precursor ion scan of the nitrophenoxy ion provides a rapid method to identify the synthesised compounds in this type of combinatorial mixture. Copyright 1999 John Wiley & Sons, Ltd.

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Section: Methodsmentioning

confidence: 99%

Effect of nitro groups and alkyl chain length on the negative ion tandem mass spectra of alkyl 3-hydroxy-5-(4′-Nitrophenoxy) and alkyl 3-hydroxy-5-(2′, 4′-dinitrophenoxy) benzoates

Kangas

Franzén

Tois

et al. 1999

Rapid Commun. Mass Spectrom.

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ChemInform Abstract: A NEW SYNTHESIS OF 3H‐PHENOXAZIN‐3‐ONES

Bird¹,

Latif²

1980

Chemischer Informationsdienst

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Reinvestigation of the Synthesis of Hydroxy‐Functionalized Diazapentacene: Unexpected Formation of a Phenoxazinone

2017

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In 1982, Buckley et al. reported on the hydroxy‐functionalized derivative of 6,13‐diazapentacene (DAP), namely 5,12‐dihydroxo‐6,13‐diazapentacene. In an attempt to reproduce the synthetic procedure, 1H NMR and 13C{1H} NMR spectroscopic data revealed the formation of a constitutional isomer of the supposed compound. A single‐crystal X‐ray structure determination revealed that the actual structure of the dark‐violet product was 6‐amino‐5H‐dibenzo[a,h]phenoxazin‐5‐one (2), a benzo[a]phenoxazine derivative. These kinds of compounds are, along with a wide range of pharmacological applications, known for their specific fluorescent properties, which were analyzed for compound 2. Furthermore, it was shown that 2 can be utilized as reagent for the synthesis of other benzo[a]phenoxazine derivatives, herein 6‐(dimethylamino)‐5H‐dibenzo[a,h]phenoxazin‐5‐one (3).

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A new synthesis of 3-phenoxazin-3-ones

Cited by 19 publications

References 11 publications

Effect of nitro groups and alkyl chain length on the negative ion tandem mass spectra of alkyl 3-hydroxy-5-(4′-Nitrophenoxy) and alkyl 3-hydroxy-5-(2′, 4′-dinitrophenoxy) benzoates

Effect of nitro groups and alkyl chain length on the negative ion tandem mass spectra of alkyl 3-hydroxy-5-(4′-Nitrophenoxy) and alkyl 3-hydroxy-5-(2′, 4′-dinitrophenoxy) benzoates

ChemInform Abstract: A NEW SYNTHESIS OF 3H‐PHENOXAZIN‐3‐ONES

Reinvestigation of the Synthesis of Hydroxy‐Functionalized Diazapentacene: Unexpected Formation of a Phenoxazinone

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