19263-30-0

Usage

InChI:InChI=1/C13H9N3O/c17-13-11-8-4-5-9-12(11)14-15-16(13)10-6-2-1-3-7-10/h1-9H

Upstream product

• 90-16-4 1,2,3-benzotriazin-4(3H)-one 
• 591-50-4 iodobenzene 
• 35358-78-2 o-methoxycarbonylbenzenediazonium chloride 
• 2385-27-5 N-phenyl-2-nitrobenzamide 
• 610-14-0 2-nitrobenzyl chloride 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 75-52-5 nitromethane 
• 4424-17-3 2-aminobenzanilide 
• 201230-82-2 carbon monoxide 
• 62-53-3 aniline 
• 615-36-1 2-bromoaniline 
• 615-43-0 2-iodophenylamine 
• 118-92-3 anthranilic acid 
• 21563-73-5 2-aminobenzoyl chloride 

Downstream Products

• 35708-19-1 Methyl N-phenylanthranilate 
• 23868-11-3 ethyl 2-(phenylamino)benzoate 
• 21119-24-4 N-Phenyl-anthranilsaeure-isopropylester 
• 21119-32-4 N-Phenyl-anthranilsaeure-β-naphthylester 
• 21119-33-5 1-(2-Phenylcarbamoyl-benzolazo)-naphthol-⁽²⁾ 
• 21119-25-5 N-t-butoxycarbonyl-L-phenylaniline 
• 21119-26-6 N,O-diphenylanthranilate 
• 21119-27-7 2-Hydroxy-4-oxo-2-methyl-1,4-dihydro-2H-3.1-benzoxazin 
• 52069-22-4 N-phenyl-anthranilic acid-anhydride 
• 93-98-1 N-phenyl benzoyl amide 
• 122082-04-6 4-oxo-3-phenyl-3,4-dihydrobenzo[d][1,2,3]triazine 1-oxide 
• 1015-89-0 6(5H)-phenanthridinone 
• 118-92-3 anthranilic acid 
• 100-63-0 phenylhydrazine 

Relevant academic research and scientific papers

Visible-light-induced denitrogenative phosphorylation of benzotriazinones: A metal- And additive-free method for accessing: Ortho -phosphorylated benzamide derivatives

Metal-free, visible-light-induced denitrogenative phosphorylation of 1,2,3-benzotriazinones was achieved. With the use of eosin Y as a photoredox catalyst, N,N-diisopropylethylamine as a base, CH3CN-H2O as a solvent and sunlight or a blue LED as a light source, a variety of aryl-phosphonates, aryl-phosphinates, and aryl-phosphine oxides were efficiently prepared. In addition, B2pin2 instead of P-nucleophiles as a radical acceptor was also demonstrated. The key advantages of this newly developed method are the clean reaction profile, use of a low-cost organic-dye catalyst, energy efficiency, broad substrate scope, good to excellent yields and large-scale synthetic applicability. The gram-scale synthesised compounds could be isolated in pure form just upon extraction, followed by re-crystallisation; no tedious chromatographic purification was required.

One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts

A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.

NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides

An efficient transformation of 2-aminobenzamides to 1,2,3-benzotriazin-4(3H)-ones in the presence of sodium nitrite (NaNO2) and Iodine (I2) is described. The reaction is proposed to proceed via formation of nitrosyl halide that induces nitrosylation of the amino group of 2-aminobenzamide leading to diazotization followed by intramolecular cyclization.

Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4-(3H)-ones with Benzynes for Construction of Phenanthridinone Scaffolds

The synthesis of phenanthridinones via denitrogenative annulation of 1,2,3-benzotriazin-4-(3H)-ones with arynes catalysed by Ni(0)/dppm was successfully developed. A variety of phenanthridinones were prepared in good to excellent yields. Based on this method, nature product, N-methylcrinasidine, was synthesized. (Figure presented.).

Selective Synthesis of 3-Arylbenzo-1,2,3-triazin-4(3H)-ones and 1-Aryl-(1H)-benzo-1,2,3-triazoles from 1,3-Diaryltriazenes through Pd(0) Catalyzed Annulation Reactions

Pd(0) catalyzed carbonylative annulation reaction of 1-(2-iodophenyl)-3-aryltriaz-1-enes in the presence of DABCO and 1 atm of carbon monoxide in toluene at 80 °C gave the corresponding 3-arylbenzo-1,2,3-triazin-4(3H)-ones with high selectivity and in exc

Potassium Iodide/tert-Butyl Hydroperoxide-Mediated Oxidative Annulation for the Selective Synthesis of N-Substituted 1,2,3-Benzotriazine-4(3H)-ones Using Nitromethane as the Nitrogen Synthon

A novel and efficient oxidative annulation of 2-aminobenzamides with nitromethane has been developed for the chemoselective synthesis of N-substituted 1,2,3-benzotriazine-4(3H)-ones in moderate to excellent yields under transition metal-free conditions. T

Cu-mediated N-arylation of 1,2,3-triazin-4-ones: Synthesis of fused triazinone derivatives as potential inhibitors of chorismate mutase

A rapid and direct access to N-aryl substituted fused triazinone derivatives has been accomplished via N-arylation of 1,2,3-triazin-4-one ring involving a Cu-mediated coupling between triazinone derivatives and aryl boronic acids. A combination of Cu(OAc)

Steric effects in the base-catalyzed cyclization of 1-[2-(methoxycarbonyl)phenyl]-3-(2-substituted phenyl)triazenes

Eleven model 1-[2-(methoxycarbonyl)phenyl]-3-(2-substituted phenyl)triazenes were synthesized and their cyclization kinetics examined in aqueous-methanolic buffer solutions (51 wt.% methanol) at various pH values. 3(2-Substituted phenyl)benzo[d][1,2,3]tri

A facile copper-catalyzed Ullmann condensation: N-arylation of heterocyclic compounds containing an -NHCO- moiety

N-Aryl heterocyclic compounds were synthesized from aryl halides and heterocyclic compounds containing an -NHCO- moiety by using a catalytic amount (1-10 mol%) of a commercially available copper catalyst in satisfactory yields. This catalytic reaction was applicable to the synthesis of N-aryl-2-pyridone, -2-pyrrolidone, -1(2H)-isoquinolone, -1(2H)- phthalazinone, -4(3H)-quinazolinone and -1,2,3-benzotriazin-4(3H)-one derivatives.

Steric effects in acid-catalyzed decomposition and base-catalyzed cyclization of 1-(2-alkoxycarbonyl-phenyl)-3-phenyltriazenes

Eight derivatives of 1-(2-alkoxycarbonylphenyl)-3-phenyltriazene (R = methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, and allyl) have been synthesized and their UV-VIS, IR, 1H and 13C NMR spectra measured. The NMR spectra have been interpreted in detail. The kinetics of acid-catalyzed decomposition and base-catalyzed cyclization of the title compounds have been measured in 52.1% w/w methanol at 25.0 °C. The unit reaction order has been verified and the cyclization product has been identified. The pH-profiles obtained have been used to calculate the catalytic rate constants kA (acid-catalyzed decomposition) and kB (base-catalyzed cyclization) of all the derivatives; the constants have been interpreted with regard to inductive and steric effects. The catalytic rate constant kA has been found to be independent of the substituents. The catalytic rate constant kB depends statistically significantly upon both inductive and steric effects, the sensitivity to the former being more significant. The experimental results and their interpretation confirm the base-catalyzed cyclization mechanism with formation of tetrahedral intermediate as the rate-limiting step.