- 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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p. 296 - 301
(2021/01/28)
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- NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides
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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.
- Barak, Dinesh S.,Mukhopadhyay, Sushobhan,Dahatonde, Dipak J.,Batra, Sanjay
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supporting information
p. 248 - 251
(2019/01/04)
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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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- Steric effects in the base-catalyzed cyclization of 1-[2-(methoxycarbonyl)phenyl]-3-(2-substituted phenyl)triazenes
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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
- Ludwig, Miroslav,Bauerova, Ingrid
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p. 2075 - 2084
(2007/10/03)
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