28230-32-2

Usage

Synthesis Reference(s)

Synthesis, p. 1008, 1990 DOI: 10.1055/s-1990-27078

InChI:InChI=1/C7H5N3O2/c11-7-5-3-1-2-4-6(5)8-9-10(7)12/h1-4,12H

Upstream product

• 5623-04-1 anthranilic hydroxamic acid 
• 60941-84-6 Sulfinamide Anhydride of Anthranilic Acid 
• 2431-91-6 4-methoxy-2,6-dimethylphenol 
• 1310558-97-4 3-benzotriazin-4-one-N-oxyl radical 
• 950-99-2 2,2,5,7,8-pentamethylchroman-6-ol 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 489-01-0 2,6-Di-t-butyl-4-methoxyphenol 
• 2374-05-2 4-bromo-2,6-dimethyl-phenol 
• 576-26-1 2.6-dimethylphenol 
• 527-60-6 Mesitol 
• 22900-79-4 N-(3,5-dimethyl-4-hydroxyphenyl)-acetamide 
• 134-20-3 2-carbomethoxyaniline 

Downstream Products

• 165534-43-0 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one 
• 28230-37-7 o-azidobenzoyl-ODhbt 
• 64908-56-1 3-benzoyloxy-1,2,3-benzotriazin-4(3H)-one 
• 442516-55-4 3-hydroxy-3,4-dihydrobenzotriazin-4-onyl α-methylcinnamate 
• 869307-75-5 N-benzyloxycarbonyl-(2S)-aminobutyric acid 3,4-dihydro-4-oxo-1,2,3-benzotriazine ester 
• 898552-43-7 4-[2-(4-Chloro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-3,3-dimethyl-butyric acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester 
• 52128-56-0 3-Acetoxy-1,2,3-benzotriazinon-4 
• 617-65-2 Glutamic acid 
• 486-25-9 9-fluorenone 
• 54769-57-2 3-benzenesulfonyloxy-3H-benzo[d][1,2,3]triazin-4-one 

Relevant academic research and scientific papers

Bifunctional Phosphine Ligand-Enabled Gold(I)-Catalyzed O-Nucleophilic Addition of N-Hydroxybenzo[1,2,3]-triazin-4(3 H)-ones to Alkynes Followed by [3,3]-Rearrangement: Simultaneous Formation of C-O and C-N Bonds

We describe a gold (I)-catalyzed tandem O-nucleophilic addition/[3,3]-rearrangement reaction of N-hydroxybenzo[1,2,3]-triazin-4(3H)-ones with alkynes enabled by a biphenyl-2-yl phosphine ligand featuring a pendant amide moiety (L1). A variety of 1-(2-oxo-2-arylethyl)benzo [d][1,2,3]triazin-4(1H)-one derivatives were synthesized in good to excellent yields. The present protocol gives a rare example of simultaneous formation of C-O and C-N bonds in the gold(I)-catalyzed [3,3]-sigmatropic rearrangements.

A Facile One-Pot Synthesis of 3,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine and Derivatives

A new one-pot synthesis of 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine (Dhbt-OH) and derivatives directly from anthranilic acids is described.The reaction of anthranilic acids and thionyl chloride affords unstable sulfinamide anhydrides which are treated with O-(trimethylsilyl)hydroxylamine followed by diazotization to give the corresponding Dhbt-OH derivatives in good overall yield.

Importance of π-stacking interactions in the hydrogen atom transfer reactions from activated phenols to short-lived N-oxyl radicals

A kinetic study of the hydrogen atom transfer from activated phenols (2,6-dimethyl- and 2,6-di-tert-butyl-4-substituted phenols, 2,2,5,7,8- pentamethylchroman-6-ol, caffeic acid, and (+)-cathechin) to a series of N-oxyl radical (4-substituted phthalimide-N-oxyl radicals (4-X-PINO), 6-substituted benzotriazole-N-oxyl radicals (6-Y-BTNO), 3-quinazolin-4-one-N-oxyl radical (QONO), and 3-benzotriazin-4-one-N-oxyl radical (BONO)), was carried out by laser flash photolysis in CH3CN. A significant effect of the N-oxyl radical structure on the hydrogen transfer rate constants (kH) was observed with kH values that monotonically increase with increasing NO-H bond dissociation energy (BDENO-H) of the N-hydroxylamines. The analysis of the kinetic data coupled to the results of theoretical calculations indicates that these reactions proceed by a hydrogen atom transfer (HAT) mechanism where the N-oxyl radical and the phenolic aromatic rings adopt a π-stacked arrangement. Theoretical calculations also showed pronounced structural effects of the N-oxyl radicals on the charge transfer occurring in the π-stacked conformation. Comparison of the kH values measured in this study with those previously reported for hydrogen atom transfer to the cumylperoxyl radical indicates that 6-CH3-BTNO is the best N-oxyl radical to be used as a model for evaluating the radical scavenging ability of phenolic antioxidants.

3-HYDROXY-4-OXO-1,2,3-TRIAZINES AND DERIVATIVES THEREOF FOR AMIDE AND ESTER BOND FORMATION

The present invention relates to the use of a compound of formula I as a coupling reagent in forming amide or ester bonds from a reaction between a carboxylic acid and an amine or an alcohol, respectively. The compounds of formula I are especially useful as coupling reagents in the preparation of peptide bonds during peptide synthesis. In particular, the compounds of formula I are useful in promoting the formation of reactive reaction intermediates, inhibiting side reactions and in suppression of racemization. In addition, the present invention provides novel compounds of Formula I, and salts of N-oxides thereof.

A 15N NMR investigation of a series of benzotriazinones and related antitumour heterocycles

A series of 3-substituted 1,2,3-benzotriazin-4-ones, 1 and 2, were synthesized by standard methods and the 15N NMR spectra were recorded. All spectra were obtained using the natural abundance of the nitrogen-15 isotope. The chemical shifts appear in the normal range for N-1, N-2 and N-3 of the triazine ring, and also correlate with the chemical shifts in the spectra of the imidazolotriazinone, 4, and the imidazolotetrazinone, 5. Significantly, the spectra of 1a, 2 and 4, recorded with full NOE, show inversion of the singlet assigned to N-3, demonstrating that these compounds exist in the tautomeric form shown. The structure of the 4-iminobenzotriazinone (3) was confirmed by this 15N NMR analysis. The spectrum shows a signal for the NH-bearing imino-nitrogen atom, which is an inverted singlet in the NOE spectrum, whereas the signal from the N-3 atom of 3 is not inverted in the NOE spectrum. Copyright