3-Hydroxyl-1,3-Diphenyltriazine as Reagent or Palladium

Sogani, N. C.; Bhattacharya, Sumanta

doi:10.1021/ac60109a026

Cited by 39 publications

(9 citation statements)

References 5 publications

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“…In Tabelle 3 sind die UV.-und 'H-NMR.-Daten von 12a-e zusammengestellt; sie sind im Einklang rnit der bisherigen Konstitutionszuordnung fur 12 [15][16][17][18] (2) [34], wird in der alteren Literatur [34] (351 als ein Tautomeres, namlich als 1,3-Diphenyltriazen-1-01 (22, R = C~HS), forrnuliert. Neueren Arbeiten zufolge [36] durfte bezeichneten Produkten die Konstitution von disubstituierten Triazen-Ioxiden 23 zukommen.…”

Section: Discussionunclassified

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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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Section: Discussionunclassified

“…Die Verbindung 23 ( R = C~H S ) , erhalten durch Kupplung von Benzoldiazoniumchlorid rnit N-Phenylhydroxylamin (20, R = C6H5) [34], wird in der alteren Literatur [34] (351 als ein Tautomeres, namlich als 1,3-Diphenyltriazen-1-01 (22, R = C~HS), forrnuliert. Neueren Arbeiten zufolge [36] Schema 9).…”

Section: ((A-l-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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“…Hydroxytriazenes based on sulpha drugs have been synthesized as per reported method (Elkins and Hunter, 1938;Sogani and Bhattacharya, 1956). This method involves reduction of nitro compounds using Zn dust in neutral medium to get corresponding hydroxylamines and its coupling with diazonium salt resulted from diazotization of sulpha drugs [Sulphathiazole (ST), Sulfisoxazole (SF) and Sulphamethoxazole (SM)] at 0-5 C, in pH 5-6 ( Figure 1).…”

Section: Synthesis Of Hydroxytriazenesmentioning

confidence: 99%

Synthesis, antidiabetic, antioxidant and anti-inflammatory activities of novel hydroxytriazenes based on sulpha drugs

Dayma

Chopra

Sharma

et al. 2020

Heliyon

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The present study is aimed to investigate the anti-inflammatory, antioxidant and antidiabetic activities of three series of hydroxytriazenes based on sulfa drugs viz; Sulphathiazole (ST), Sulfisoxazole (SF) and Sulphamethoxazole (SM). Antidiabetic activities of the synthesized hydroxytriazenes were investigated by α-glucosidase and α-amylase inhibition method and IC 50 values were recorded. The compounds presented significant α-glucosidase and α-amylase inhibition effect with IC 50 values ranging from 122 to 341 μg/mL. Anti-inflammatory activity was also investigated by carrageenan-induced paw edema (CPE) method, where % inhibition was up to 89% after 4 h of treatment and antioxidant properties of the similar compounds were assessed by DPPH and ABTS radical scavenging assays. Antioxidant capacity of all the hydroxytriazenes detected by ABTS assay, was significantly higher as compared to DPPH assay. The hydroxytriazenes having highest antioxidant capacity presented IC 50 values for compound ST-1 and ST-6 are 488 μg/mL for DPPH, 54.12 μg/mL for ABTS and 858.5 μg/mL for DPPH, 48.0 μg/mL for ABTS, respectively. These results suggested that ABTS assay may be more useful than DPPH assay for synthetic antioxidants. The findings from the molecular docking experiments may also expand the formation of new potent sulpha drugs based hydroxytriazenes targeting towards the subunit of C-terminal of human maltaseglucoamylase for the treatment of diabetes metabolic disorder. Overall, highlight the multifunctional role of hydroxytriazenes as antidiabetic, antioxidant and anti-inflammatory agents.

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“…All the nine hydroxytriazenes have been synthesized by the method as reported in the literature [9][10][11][12][13][14] . The method involves preparation of aryl or alkyl hydroxylamine, aryldiazonium salts and coupling them at the temperature between 0-5ºC.…”

Section: Synthesis Of Hydroxytriazenesmentioning

confidence: 99%

Studies on Insecticidal Activity of Some Hydroxytriazene Derivatives

Kumar

Garg

Jodha

et al. 2008

Journal of Chemistry

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Nine hydroxytriazenes have been synthesized and screened for their insecticidal activity against one day oldDrosophila melanogasterMeig (Fruit fly). Out of all the nine compounds screened, 3-hydroxy-3-n-propyl-1-m-chlorophenyltriazene is the most active having LC50values 0.9847 ppm. The least active compound is 3-hydroxy -3-n-propyl-1-p-methylphenyltriazene, whose values are 16.52 ppm. In general, the LC50values range from 3.92 to 5.52 ppm.

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3-Hydroxyl-1,3-Diphenyltriazine as Reagent or Palladium

Cited by 39 publications

References 5 publications

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

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

Synthesis, antidiabetic, antioxidant and anti-inflammatory activities of novel hydroxytriazenes based on sulpha drugs

Studies on Insecticidal Activity of Some Hydroxytriazene Derivatives

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