- 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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- Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita
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A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L?1 in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L?1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further.
- Chen, Xiulei,Zhou, Zhen,Li, Zhong,Xu, Xiaoyong
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p. 194 - 200
(2019/09/13)
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- Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole against Meloidogyne incognita
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Based on the characteristic of benzo[d][1,2,3]thiadiazole to induce the systemic acquired resistance and improve the immunity of plants, benzo[d][1,2,3]thiadiazole was introduced into 1,2,3-benzotriazin-4-one, thirty-one novel 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole were designed and synthesized. Nematicidal activity showed that most of the synthesized compounds exhibited great inhibitory activity in vivo against Meloidogyne incognita at 20 mg/L. Among 31 tested compounds, A2 and A3 showed an excellent nematicidal activity with the inhibition rate of 50.4percent and 53.1percent at the concentration of 1.0 mg/L, respectively. The influence of substituent type and position was investigated. The relationship between structure and activity was also preliminary analyzed.
- Chen, Xiulei,Guo, Wei,Li, Zhong,Wang, Gaolei,Xu, Xiaoyong,Zhang, Ruifeng
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supporting information
(2020/07/10)
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- Redox Cyclization of Amides and Sulfonamides with Nitrous Oxide for Direct Synthesis of Heterocycles
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Herein we report a redox cyclization of amides and sulfonamides with nitrous oxide (N2O) for the direct synthesis of heterocycles. Various amides and sulfonamides could undergo directed ortho metalation (DoM) by treatment with BuLi, and the lithium intermediate could be trapped by N2O gas to achieve redox cyclization. N2O serves as a N-atom donor to mediate the intramolecular coupling of lithium species toward heterocycle formation with free external oxidant. This protocol offers a direct synthesis of heterocycles with features of readily available starting materials, simple operation, and a broad substrate scope.
- Lai, Zhencheng,Wang, Chaorong,Li, Jiaming,Cui, Sunliang
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p. 2017 - 2021
(2020/03/04)
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- Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles
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We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.
- Bi, Hong-Yan,Li, Cheng-Jing,Liang, Cui,Mo, Dong-Liang,Wei, Cui
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p. 5815 - 5821
(2020/09/21)
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- Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker against Meloidogyne incognita
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To explore new skeleton with nematicidal activity, a series of novel 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker were synthesized and varied fragments were also introduced to increase structure diversity of the new skeleton. Their inhibitory activities in vivo were evaluated against Meloidogyne incognita. The newly prepared compounds A6, A8, A21, A28 and A38 exhibited more than 50% inhibition at the concentration of 20 mg/L. Especially compound A6 displayed 71.4% inhibition against Meloidogyne incognita at the concentration of 20 mg/L. The nematicidal activities varied significantly depending on the types and positions of the substituents, which provided guidance for further structure modification.
- Chen, Xiulei,Jia, Haowu,Li, Zhong,Xu, Xiaoyong
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p. 1207 - 1213
(2019/03/29)
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- A benzene and three qinqin alkone of 1, 4 - pentadiene -3 - ketone derivatives, preparation method and use thereof
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The invention discloses a 1,4-pentadiene-3-ketone derivative containing benzotriazinone. The 1,4-pentadiene-3-ketone derivative containing benzotriazinone is characterized by having the general formula as shown in the specification, wherein R1 is phenyl, substituted phenyl (p-fluorophenyl, p-chlorophenyl, o-chlorophenyl, 2-methyoxyphenyl, 4-methyoxyphenyl, 4-methylphenyl, 2,4-dimethyoxyphenyl, 3,4-dimethyoxyphenyl, cinnamaldehyde group, 3-nitrophenyl, 2-chloro-5-nitrophenyl and the like), heterocyclic group (furyl, thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrryl and the like) or substituted aromatic heterocyclic group (5-methyl thiazole, 5-methyl-2-thienyl, 4-bromo-2-thienyl and the like), and R2 is a hydrogen atom, methyl (ethyl), methoxyl (ethyoxyl) and the like. The compound disclosedby the invention has relatively high inhibiting activity for citrus canker bacteria, ralstonia solanacearum and tobacco mosaic viruses so as to be used for preparing an agricultural bactericide and anantiviral agent.
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Paragraph 0038; 0042
(2019/11/12)
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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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- Nitrogenous heterocyclic compound with nematocidal activity, preparation method and application thereof
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The invention relates to a nitrogenous heterocyclic compound with nematocidal activity, a preparation method and application thereof. Specifically, the invention discloses a compound with a formula (I) or an optical isomer, cis-trans isomer or acceptable salt in agricultural pharmacology and a preparation method thereof. The invention further discloses an agricultural composition containing the compound and application thereof. The compound has excellent nematocidal activity.
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Paragraph 0141; 0142; 0143
(2018/07/30)
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- Synthesis, antibacterial, and antiviral activities of novel penta-1,4-dien-3-one derivatives containing a benzotriazin-4(3H)-one moiety
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A series of penta-1,4-dien-3-one containing a benzotriazin-4(3H)-one moiety were prepared and evaluated for their antibacterial and antiviral activities. Bioassays indicated that some compounds exhibited good antibacterial and antiviral activities. Among them, the EC50 values of compound 6d against Xanthomonas axonopodis pv. citri and compound 6l against Ralstonia solanacearum were, respectively, 22.45 and 34.77?μg/mL, which were better than that of thiodiazole copper (51.35 and 87.26?μg/mL, respectively). Meanwhile, some title compounds were found to show remarkable antiviral activities against tobacco mosaic virus (TMV). These results indicated that penta-1,4-dien-3-one derivatives containing benzotriazin-4(3H)-one moiety could play significant roles in searching for novel agrochemicals.
- Zhang, Ju-Ping,Li, Qin,Zhang, Cheng,Li, Pu,Chen, Li-Juan,Wang, Yi-Hui,Ruan, Xiang-Hui,Xiao, Wei,Xue, Wei
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p. 2193 - 2202
(2018/08/06)
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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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supporting information
p. 6494 - 6497
(2018/10/20)
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- Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea against Meloidogyne incognita
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Two series of novel 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea were designed and synthesized. The bioassay results showed that most of the test compounds showed good nematicidal activity against M. incognita at the concentration of 10.0?mg?L?1 in vivo. The compounds A13, A17 and B3 showed excellent nematicidal activity on the second stage juveniles of the root-knot nematode with the inhibition rate of 51.3%, 58.3% and 51.3% at the concentration of 1.0?mg?L?1 respectively. It suggested that the structure of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea could be optimized further.
- Chang, Yaning,Zhang, Jingwei,Chen, Xiulei,Li, Zhong,Xu, Xiaoyong
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supporting information
p. 2641 - 2644
(2017/05/10)
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- Synthesis and biological evaluation of novel 1,2,3-benzotriazin-4-one derivatives as leukotriene A4 hydrolase aminopeptidase inhibitors
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A series of novel 1,2,3-benzotriazin-4-one derivatives were designed, synthesized and their inhibitory activities against leukotriene A4 hydrolase aminopeptidase in vitro were evaluated. Many compounds showed moderate to good activities at the concentration of 10?μmol/L. Among them, compound IV-16 exhibited the highest inhibitory activity up to 80.6% with an IC50 of 1.30?±?0.20?μmol/L. The compound IV-16 was also tested the proliferation inhibitory activities in THP1 human AML cell line and its binding model with LTA4H enzyme by molecular docking was studied. It indicated that 1,2,3-benzotriazin-4-one was a promising scaffold for further study. The relationship between structure and inhibitory activity was also preliminarily discussed.
- Zhang, Fan,Wu, Dang,Wang, Gao-Lei,Hou, Shuang,Ou-Yang, Ping,Huang, Jin,Xu, Xiao-Yong
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supporting information
p. 1044 - 1048
(2017/05/22)
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- Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against Meloidogyne incognita
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A series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized by the reaction of 3-bromoalkyl-1,2,3-benzotriazin-4-ones with potassium salt of 2-cyanoimino-4-oxothiazolidine in the presence of potassium iodide. Nematicidal assays in vivo showed that some of them exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita, up to 100% at the concentration of 10.0 mg L-1, which indicated that 1,2,3-benzotriazin-4-one derivatives might be potential for novel promising nematicides. The nematicidal activity was influenced by the combination of substituent type, substituted position, and linker length in the molecule. The inhibition rate data at the concentrations of 5.0 and 1.0 mg L-1 for the compounds with high inhibitory activities were also provided. When tested in vitro, none of them showed direct inhibition against M. incognita. The investigation of a significant difference between in vivo and in vitro data is in progress.
- Wang, Gaolei,Chen, Xiulei,Deng, Yayun,Li, Zhong,Xu, Xiaoyong
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p. 6883 - 6889
(2015/08/18)
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- Synthesis of 1,2,3-benzotriazin-4-one derivatives containing spirocyclic indoline-2-one moieties and their nematicidal evaluation
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To discover new chemotypes of nematicides with proper toxicological profiles, a series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized and further bioevaluated. The bioassay results showed that most of the synthesized compounds were endowed with moderate to good control efficacy against Meloidogyne incognita at 10.0 mg/L in vivo. Among them, compounds 6k and 6p displayed 100% inhibitory activities at this concentration, which implied that they could be used as lead compounds for promising nematicides.
- Wang, Gao-Lei,Chen, Xi,Chang, Ya-Ning,Du, Dan,Li, Zhong,Xu, Xiao-Yong
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supporting information
p. 1502 - 1506
(2015/12/23)
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- A 15N NMR investigation of a series of benzotriazinones and related antitumour heterocycles
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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
- Vaughan, Keith,Wilman, Derry E. V.,Wheelhouse, Richard T.,Stevens, Malcolm F. G.
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p. 300 - 302
(2007/10/03)
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- Nitrosation with Sodium Hexanitrocobaltate(III)
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Na3Co(NO2)6 has been investigated as a new reagent for the nitrosation of various substrates containing an amino functionality. Reactions took place in an aqueous solution of the reagent. The pH of the reaction mixture remained in the range 4.3-5. Thus, hydrazides were transformed to the corresponding acyl azides, and the reactions with arenesulfonyl hydrazines afforded arenesulfonyl azides. Treatment of aromatic amines with Na3Co(NO2)6 gave 1,3-diaryltriazenes in excellent yields; coupling of the initially formed diazo compound to the electron rich aromatic ring was also observed. Nitrosation of aliphatic amines was not possible due to complex formation with the reagent.
- Stefane, Bogdan,Kocevar, Marijan,Polanc, Slovenko
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p. 7165 - 7169
(2007/10/03)
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- PREPARATION OF OLIGONUCLEOTIDES CONTAINING dAICA USING AN UNEXPECTED SIDE-REACTION OBSERVED ON A PROTECTED DERIVATIVE OF 2-AZA-2'-DEOXYINOSINE.
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Attempts of synthesis of oligonucleotides containing 2-aza-2'-deoxyinosine protected with the N,N-diphenylcarbamoyl group are described.An unexpected behaviour of the protected nucleoside can be used for the introduction of dAICA in synthetic oligonucleotides.
- Fernandez-Forner, Dolors,Eritja, Ramon,Bardella, Francesc,Ruiz-Perez, Catalina,Solans, Xavier,et al.
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p. 8917 - 8930
(2007/10/02)
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- 1,2,3-benzotriazinone 1-oxides
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3-Substituted 1,2,3-benzotriazin-4(3H)-one 1-oxides are formed on peracid oxidation of 3-alkyl- and 3-methoxy-1,2,3-benzotriazin-4(3H)-ones. The 3-(a-alkoxyalkyl) 1-oxide derivatives could be dealkylated to the tautomeric 3-unsubstituted compound. The acidities of the isomeric N-oxides of the 1,2,3-benzotriazinone system are compared. Phenyl iodosodiacetate converts o-nitrobenzaldehyde benzyl- and phenyl-hydrazones into the 2-substituted 4-oxido-1,2,3-benzotriazine1 -oxide betaines(1).
- Boulton,Devi, Purabi,Henderson, Neil,Jarrar, Adil A.,Kiss, Miklos
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p. 543 - 546
(2007/10/02)
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- Photochemistry of Pesticides, 10. Photodegradation of O,O-Diethyl-S(3,4-dihydro-4-oxobenzotriazin-3-yl-methyl)phosphorodithioate (Azinphos-ethyl)
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The photodegradation of Azinphos-ethyl (1) in chloroform and methanol solution has been studied. 3,4-Dihydro-3-methyl-4-oxobenzotriazine (3), 3,4-dihydro-4-oxo-benzotriazine (5), O,O-diethyl-O(3-methylbenzotriazine-4-yl)phosphate (8), N-methylanthranilic acid (11) (in methanol: methyl ester 12), and sulfur have been isolated and characterized as photoproducts.The decay mechanism is discussed. - Azinphos Ethyl, Photodegradation, 4-Oxobenzotriazines, O-Phosphates, N-Methyl-anthranilic Acid
- Abdou, W. M.,Sidky, M. M.,Wamhoff, H.
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p. 907 - 910
(2007/10/02)
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- Synthesis of Some N3-Aryl (or Heteroaryl)-Azo-1,2,3-Benzotriazin-4-ones
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A series of N3-aryl (or heteroaryl)-azo-1,2,3-benzotriazin-4-ones was prepared by coupling of 3H-1,2,3-benzotriazin-4-one with a series of aromatic or heteroaromatic diazonium salts.The coupling was found to occur at the N3 atom.
- El-Shafei, A. K.,Ghattas, A. A. G.
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- Synthesis and antimicrobial activity of some anthranilic acid derivatives.
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The synthesis of eight derivatives of anthranilic acid is described. Investigation of their antimicrobial activity showed that four of the compounds, viz; anthranilohydrazide, 3,4-dihydro-4-oxo-1,2,3-benzotriazine, triazine-beta-naphthol adduct and N-phenyl anthranilic acid showed significant antibacterial activity. None of the compounds showed any noticeable antifungal effect.
- Kar,Gugnani,Madumere
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p. 466 - 468
(2007/10/02)
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