- One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts
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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.
- Faggyas, Réka J.,McGrory, Rochelle,Sutherland, Andrew
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p. 6127 - 6140
(2021/07/21)
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- Visible-light-induced denitrogenative phosphorylation of benzotriazinones: A metal- And additive-free method for accessing: Ortho -phosphorylated benzamide derivatives
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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.
- Chen, Fushan,Hu, Shanshan,Li, Sipei,Tang, Guo,Zhao, Yufen
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supporting information
p. 296 - 301
(2021/01/28)
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- Ni-Catalyzed Denitrogenative Cross-Coupling of Benzotriazinones and Cyclopropanols: An Easy Access to Functionalized β-Aryl Ketones
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A novel Ni-catalyzed denitrogenative cross-coupling between benzotriazinones and cyclopropanols is reported herein. This neoteric reactivity allows for the convenient synthesis of β-(o-amido)aryl ketones from readily available starting materials with good yields (up to 93percent) and general substrate scope.
- Li, Jincan,Zheng, Yan,Huang, Mingxian,Li, Wanfang
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p. 5020 - 5024
(2020/07/03)
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- Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4-(3H)-ones with Benzynes for Construction of Phenanthridinone Scaffolds
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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.).
- Thorat, Vijaykumar H.,Upadhyay, Nitinkumar Satyadev,Murakami, Masahiro,Cheng, Chien-Hong
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p. 284 - 289
(2017/12/26)
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- 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
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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
- Khaligh, Nader Ghaffari,Johan, Mohad Rafie,Ching, Juan Joon
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p. 186 - 189
(2018/03/09)
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- Oxidative Rearrangement of 3-Aminoindazoles for the Construction of 1,2,3-Benzotriazine-4(3 H)-ones at Ambient Temperature
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A novel oxidative rearrangement of 3-aminoindazoles is reported, enabling the production of diverse functionalized 1,2,3-benzotriazine-4(3H)-ones in good yields at room temperature. The key success of this unprecedented transformation of 3-aminoindazoles is the use of water as cosolvent, which could facilitate the halogen-induced ring expansion of 3-aminoindazoles under oxidative conditions.
- Zhou, Yao,Wang, Ya,Lou, Yixian,Song, Qiuling
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p. 6494 - 6497
(2018/10/20)
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- 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
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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
- Chandrasekhar, Attoor,Sankararaman, Sethuraman
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p. 11487 - 11493
(2017/11/10)
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- 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
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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
- Yan, Yizhe,Li, Hongyi,Niu, Bin,Zhu, Changrui,Chen, Ting,Liu, Yanqi
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supporting information
p. 4170 - 4173
(2016/08/24)
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- 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
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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
- Yan, Yizhe,Niu, Bin,Xu, Kun,Yu, Jianhua,Zhi, Huanhuan,Liu, Yanqi
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supporting information
p. 212 - 217
(2016/02/14)
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- Preparation method of N-substituted 1,2,3-phentriazine-4-ketone
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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
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Paragraph 0018; 0019; 0020
(2016/10/08)
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- Enantioselective synthesis of 3,4-dihydroisoquinolin-1(2H)-ones by nickel-catalyzed denitrogenative annulation of 1,2,3-benzotriazin-4(3H)-ones with allenes
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(Chemical Equation Presented) A denitrogenative annulation reaction of 1,2,3-benzotriazin-4(3H)-ones with allenes catalyzed by a nickel-phosphine complex to produce a variety of substituted 3,4-dihydroisoquinolin-1(2H)-ones in a regioselective manner is described. A highly enantioselective version, as well as structural evidence for the mechanistic course of this reaction, is also presented.
- Yamauchi, Motoshi,Morimoto, Masao,Miura, Tomoya,Murakami, Masahiro
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supporting information; experimental part
p. 54 - 55
(2010/03/25)
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- Nickel-catalyzed denitrogenative annulation reactions of 1,2,3-Benzotriazin-4(3 H)-ones with 1,3-dienes and alkenes
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(Figure presented) 1,2,3-Benzotriazin-4(3H)-ones react with 1,3-dienes in the presence of a nickel(0)/phosphine complex to give a variety of 3,4-dihydroisoquinolin-1(2H)-ones. Oxidative insertion of nickel(0) into the triazinone moiety prompts extrusion of dinitrogen to give a five-membered ring azanickelacyclic intermediate. Subsequent insertion of 1,3-dienes into the nickel-carbon bond followed by allylic amidation affords 3,4-dihydroisoquinolin- 1(2H)-ones. Alkenes also undergo insertion into the five-membered ring azanickelacyclic intermediate, and subsequent reductive elimination gives 3-substituted 3,4-dihydroisoquinolin-1(2H)-ones.
- Miura, Tomoya,Morimoto, Masao,Yamauchi, Motoshi,Murakami, Masahiro
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supporting information; experimental part
p. 5359 - 5362
(2010/10/04)
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- SYNTHESIS AND CYCLIZATION KINETICS AND MECHANISM OF 1-(2-ETHOXYCARBONYLPHENYL)-3-ARYLTRIAZENES. KINETIC ACIDITY FUNCTION OF SODIUM METHOXIDE IN METHANOL
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Eight 1-(2-ethoxycarbonylphenyl)-3-aryltriazenes have been synthetized and the rate constants of their sodium-metoxide-catalyzed cyclization have been measured in methanol at 25.0 deg C.The experimental rate constants kobs have been adopted to construct the kinetic acidity function HKM which has been shown to be identical with the -log -> values.Two mathematical procedures have been used to determine the catalytic rate constants and their dependence on the Hammett substituent constants.A closer dependence is obtained with the ? values than with the?p- values.The Q value found (0.3) indicates a compensation of the substituent effects upon the dissociation of the starting triazene and upon the subsequent reaction of the conjugated base.Out of the two mechanistic alternatives - E1cB and BAc2 - the latter appears to be more probable, the splitting of tetrahedral intermediate being its limiting step.
- Pytela, Oldrich,Dlouhy, Vladimir
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p. 2468 - 2474
(2007/10/02)
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