15561-72-5Relevant 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.
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
, 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.).
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
Preparation method of N-substituted 1,2,3-phentriazine-4-ketone
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Paragraph 0060; 0061; 0062, (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
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
Synthesis of 1(2H)-isoquinolones by the nickel-catalyzed denitrogenative alkyne insertion of 1,2,3-benzotriazin-4(3H)-ones
Miura, Tomoya,Yamauchi, Motoshi,Murakami, Masahiro
supporting information; experimental part, p. 3085 - 3088 (2009/04/12)
(Chemical Equation Presented) 1,2,3-Benzotriazin-4(3H)-ones reacted with internal and terminal alkynes in the presence of a nickel(0)/phosphine catalyst to give a wide range of substituted 1(2H)-isoquinolones in high yield. The reaction proceeded through denitrogenative activation of the triazinone moiety and the following insertion of alkynes.
A 15N NMR investigation of a series of benzotriazinones and related antitumour heterocycles
Vaughan, Keith,Wilman, Derry E. V.,Wheelhouse, Richard T.,Stevens, Malcolm F. G.
, p. 300 - 302 (2007/10/03)
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
Microwave synthesis and anticonvulsant activity of new 3-benzyl-1,2,3- benzotriazin-4(3H)-ones
Kornet
, p. 1391 - 1393 (2007/10/03)
Several 3-benzyl-1,2,3-benzotriazin-4(3H)-ones 1 were prepared by alkylation of 1,2,3-benzotriazin-4(3H)-one with benzyl halides in dimethylformamide in a microwave oven in moderate yields. Accompanying 1 were minor amounts of products believed to be the O-alkylated derivatives. Support for 3-benzylation is shown by an alternate synthesis of 1a from o-amino-N- benzylbenzamide by nitrous acid cyclization. The title compounds were evaluated in mice and rats in maximal electroshock (MES) and pentylenetetrazole (scMet) seizure models for anticonvulsant activity, and in the rotorod test for neurotoxicity. They were generally non-toxic. The 3- benzyl analog was the most active (maximal electroshock) compound; it's maximal electroshock ED50 value was 93 mg/kg (mouse).
