54970-85-3Relevant academic research and scientific papers
One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts
Faggyas, Réka J.,McGrory, Rochelle,Sutherland, Andrew
, p. 6127 - 6140 (2021/07/21)
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.
Visible-light-induced denitrogenative phosphorylation of benzotriazinones: A metal- And additive-free method for accessing: Ortho -phosphorylated benzamide derivatives
Chen, Fushan,Hu, Shanshan,Li, Sipei,Tang, Guo,Zhao, Yufen
supporting information, p. 296 - 301 (2021/01/28)
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.
Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4-(3H)-ones with Benzynes for Construction of Phenanthridinone Scaffolds
Thorat, Vijaykumar H.,Upadhyay, Nitinkumar Satyadev,Murakami, Masahiro,Cheng, Chien-Hong
supporting information, p. 284 - 289 (2017/12/26)
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.).
Saccharin and tert-Butyl Nitrite: Cheap and Efficient Reagents for the Synthesis of 1,2,3-Benzotriazine-4-(3H)-ones from 2-Aminobenzamides under Metal-Free Conditions
Khaligh, Nader Ghaffari,Johan, Mohad Rafie,Ching, Juan Joon
, p. 186 - 189 (2018/03/09)
A mild and eco-friendly protocol for the synthesis of 1,2,3-benzotriazine-4-(3H)-ones is described using saccharin as a cheap and efficient catalyst and tert-butyl nitrite as a diazotization reagent for the first time. The current method has advantages su
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
Chandrasekhar, Attoor,Sankararaman, Sethuraman
, p. 11487 - 11493 (2017/11/10)
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
Preparation method of N-substituted 1,2,3-phentriazine-4-ketone
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Paragraph 0024; 0025; 0026, (2016/10/08)
The invention discloses a preparation method of N-substituted 1,2,3-phentriazine-4-ketone. The preparation method specifically comprises the following step: by taking anthranilamide as a reaction substrate, taking tert-butyl nitrite as a nitrogen source a
Mild and efficient TBAI-catalyzed synthesis of 1,2,3-benzotriazine-4-(3H)-ones from tert-butyl nitrite and 2-aminobenzamides under acid-free conditions
Yan, Yizhe,Li, Hongyi,Niu, Bin,Zhu, Changrui,Chen, Ting,Liu, Yanqi
supporting information, p. 4170 - 4173 (2016/08/24)
A facile and efficient annulation of 2-aminobenzamides and tert-butyl nitrite was developed, affording 1,2,3-benzotriazine-4-(3H)-ones in good yields under mild conditions. Notably, the reaction was carried out in the absence of strong acid and tert-butyl
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
Yan, Yizhe,Niu, Bin,Xu, Kun,Yu, Jianhua,Zhi, Huanhuan,Liu, Yanqi
supporting information, p. 212 - 217 (2016/02/14)
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
Steric effects in the base-catalyzed cyclization of 1-[2-(methoxycarbonyl)phenyl]-3-(2-substituted phenyl)triazenes
Ludwig, Miroslav,Bauerova, Ingrid
, p. 2075 - 2084 (2007/10/03)
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
