Notiz über Formylphenylhydrazin

Bamberger, Eug.

doi:10.1002/cber.18970300219

Cited by 26 publications

(23 citation statements)

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“…General: NMR spectra were obtained on a Varian INOVA spectrometer operating at 500 MHz for 1 H NMR, 126 MHz for 13 C NMR and 282 MHz for 19 F NMR, or on a Varian UNITY 300 spectrometer operating at 300 MHz for 1 H NMR and 75 MHz for 13 C NMR (selected NMR spectra are given in the Supporting Information). Two-dimensional NMR experiments including COSY and HSQC were used to assign the spectra, and were obtained on the Varian INOVA spectrometer operating at 500 MHz.…”

Section: Methodsmentioning

confidence: 99%

“…Solid Na 2 CO 3 was added until effervescence ceased and the aqueous layer was basic to litmus. The aqueous layer was back-extracted with CH 2 Cl 2 and the combined organics were washed with 10 % aqueous HCl, saturated aqueous NaHCO 3 (E)-[N-(1-Benzyl-3,3,3-trifluoro-2-hydroxypropyl)-4-(4-iodophenylazo)benzenesulfonamide] (23): A suspension of 19 (130 mg, 0.34 mmol) and 4-iodonitrosobenzene 21 [12,13] (79 mg, 0.34 mmol) in AcOH (1.5 mL) was stirred at 100 8C for 4 h. The reaction mixture was cooled to RT then diluted with water/CH 2 Cl 2 (1:1, 50 mL). Solid Na 2 CO 3 was added until effervescence ceased and the aqueous layer was basic to litmus.…”

Section: Synthesismentioning

confidence: 99%

“…nitrosobenzene to form the azobenzene moiety and oxidation to give the trifluoromethylketone. In particular, compounds 6 and 7 were prepared by coupling of 4-nitrosulfonyl chloride 17 to 11 a to give sulfonamide 18, catalytic reduction to 19, condensation with nitrosobenzenes 20 [10,11] and 21 [12,13] to give the azobenzenes 22 and 23, respectively, and finally oxidation using TEMPO to give ketones 6 and 7, respectively. Compounds 8 and 9 were similarly prepared, using 3-nitrosulfonyl chloride 24 as starting material instead of 17.…”

Section: Scheme 2 Synthesis Ofmentioning

confidence: 99%

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Improved Photocontrol of α‐Chymotrypsin Activity: Peptidomimetic Trifluoromethylketone Photoswitch Enzyme Inhibitors

Pearson

Alexander

Abell

2008

Chemistry A European J

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A series of peptidomimetic trifluoromethylketones containing the photoisomerisable azobenzene group have been synthesised, photoisomerised and assayed against the serine protease alpha-chymotrypsin. All are inhibitors of the enzyme and exhibit up to a fivefold increase in activity on UV irradiation. Visible irradiation returns activity to close to that of the original sample. These results suggest the trifluoromethylketone group to be the best electrophilic enzyme binding group for use in photoswitch inhibitors of alpha-chymotrypsin.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Section: Scheme 2 Synthesis Ofmentioning

confidence: 99%

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Improved Photocontrol of α‐Chymotrypsin Activity: Peptidomimetic Trifluoromethylketone Photoswitch Enzyme Inhibitors

Pearson

Alexander

Abell

2008

Chemistry A European J

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“…The self-condensation of o-aminobenzaldehyde, OAB, (4), under acidic conditions was first investigated in the 1920s by Seidel (1926Seidel ( , 1927 and by Bamberger (1927). Despite extensive studies, the structures of the acid condensation products remained controversial.…”

Section: Introductionmentioning

confidence: 99%

Structural investigation of the self-condensation products of o-aminobenzaldehyde, anthranilic acid and related compounds. 1. The TAAB salts TAABH₂ X ₂ [X = picrate (ordered), HSO₄ (disordered) and BF₄ (disordered)]. Hydrogen bonding and the importance of two non-equivalent lone-pair donor sites in the anion for order

Owston¹,

Shaw²

1988

Acta Crystallogr Sect B

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“…Das zur Offnung von Imidringen im Sinne der zweiten Stufe von Gabriel-Synthesen von primaren Aminen[48] gebrauchliche Hydrazin bot sich als Reagens an. Durch Hydrazinolyse nach Eschenmoser et al[4] entstand aus 14a, 14b sowie 14f unter Gasentwicklung neben N , N'-Phthaloylhydrazin(39), anstelle des erwarteten und vermutlich auch als Primarprodukt intermediar auftretenden monosubstituierten Triazen-1-oxids 40, in hohen Ausbeuten (> 95%) ein N-substituiertes Hydroxylamin 20. Die Bildung von 20 laisst sich uber eine Tautomerisierung von 40 zu einem Triazen-1-0141 erklaren, dessen monosubstituierte Diazen-Teilstruktur dafiir pradestiniert ist, N, zu verlieren (vgl [49]…”

unclassified

1‐Aryl‐ und 1‐Alkyl‐2‐phthalimido‐diazen‐1‐oxide, diacylierte Vertreter von trisubstituierten Triazen‐1‐oxiden: Bildung, Eigenschaften, Stereoisomerisierung und Fragmentierung

Hoesch

Köppel

1981

Helvetica Chimica Acta

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1-Aryl-and l-Alkyl-2-phthalimido-diazene-l-oxides, Diacylated Examples of TrisubstitutedTriazene-1-oxides: Formation, Properties, Stereoisomerizalion and Fragmentation') SummaryOxidatively generated phthalimido-nitrene (1) reacts with nitrosobenzene @a), p-nitrosotoluene (Sb), o-nitrosotoluene (Sc), p-dimethylamino-nitrosobenzene (Sd), p-methoxycarbonyl-nitrosobenzene (Se), I, 1-dimethyl-1 -nitrosoethane (Sf) and nitrosocyclohexane (8g) to give the respective 1-substituted (2)-2-phthalimidodiazene-I-oxides 14a-g.The constitution of the 2-imidodiazene-1-oxides 14 is deduced from their spectroscopic properties. The UV. spectra of 14a-e are similar with those of the corresponding nitrobenzenes 18, thus supporting the concept of comparibility of the phthalimido-N group with an 0-atom and indicating that the phthalimido group is not in conjugation with the diazene-oxide function. This is in contrast to the situation in the non-acylated trisubstituted triazene-1-oxides 12, where conjugation is extended over the chain of all three N-atoms as exhibited by the UV. spectra of (2)-I13,3-triphenyl-, (2)-3,3-dimethyl-1-phenyl-, (Z)-3-methyl-1,3-diphenyl-, (2)-l-(l,l-dimethylethyl)-3,3-diphenyl-, and (Z)-1-(l,l-dimethylethyl)-3,3-dimethyltriazene-1-oxide (12a-e). These triazene-1-oxides are formed by the reaction of 1,l-disubstituted hydrazines 11 with three mol-equiv. of nitroso compounds 8 or from equimolar amounts of 11 and 8 in the presence of mercury oxide. Over 90% of 1,2-diphenyIdiazeneoxide (19, R = C6H5) are isolated by the reaction 11+3 8a. Possible mechanisms of the reaction of 11 with 8, and of the formation of 12 via triazanols D and of 19 (R=C6HS) via N-phenylhydroxylamine (20, R=C6H5) are given in Scheme 6 (in the latter case with experimental evidence). An independent synthesis of 12c confirms the constitutional assignment for 12. ') , 3,

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Notiz über Formylphenylhydrazin

Cited by 26 publications

References 1 publication

Improved Photocontrol of α‐Chymotrypsin Activity: Peptidomimetic Trifluoromethylketone Photoswitch Enzyme Inhibitors

Improved Photocontrol of α‐Chymotrypsin Activity: Peptidomimetic Trifluoromethylketone Photoswitch Enzyme Inhibitors

1‐Aryl‐ und 1‐Alkyl‐2‐phthalimido‐diazen‐1‐oxide, diacylierte Vertreter von trisubstituierten Triazen‐1‐oxiden: Bildung, Eigenschaften, Stereoisomerisierung und Fragmentierung

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