27556-51-0Relevant articles and documents
Oxidative dehydrocoupling of N-H bonds using a redox-active main group superbase
Less, Robert J.,Naseri, Vesal,McPartlin, Mary,Wright, Dominic S.
, p. 6129 - 6131 (2011)
Reaction of the redox-active base Sn(NMe2)2/ nBuLi with o-phenylene diamine leads to oxidative dehydrocoupling and rearrangement into the triazolyl anion.
Hydrolysis of N-cyanoazoles
Pan'kov,Belyakova,Vishnyakov,Purygin
, p. 763 - 766 (2001)
The hydrolysis kinetics of N-cyanoazoles in alkaline solutions is described by a first-order kinetic equation with respect to the substrate and concentration of hydroxide ions. The hydrolysis rate constants increase with increasing number of nitrogen atoms in the heterocyclic moiety and decrease with introduction of the annelated benzene ring.
Selective addition reactions of difluoromethyltriazoles to ketones and aldehydes without the formation of difluorocarbene
Chai, Jin Young,Cha, Hyojin,Kim, Hyeong Baik,Chi, Dae Yoon
, (2020)
There has been great interest in the chemistry, syntheses and reactivities of heteroaryl-N-difluoromethane. The present work is based on the addition reaction of difluoromethyl anions, which are generated directly from difluoromethyl heterocycles, to benzophenone and benzaldehyde. As 1,2,3-triazoles and benzotriazoles can act as leaving groups, two reaction pathways are expected to exist: either the desired reaction route - deprotonation (formation of difluoromethyl anion) or the unfavored reaction route – the formation of difluorocarbene. We describe the chemistry for the selective addition reactions of difluoromethyltriazoles to ketones and aldehydes without the formation of difluorocarbene. Addition reactions of 1-(difluoromethyl)-1H-benzotriazole 1 to benzophenone 2 using potassium t-butoxide as a base were found to proceed smoothly at 0 °C for 5 min with high yields (80–88percent). A plausible mechanism for the addition reactions of 1-(difluoromethyl)-1H-benzotriazole 1 and 1-difluoromethyl-4-phenyltriazole 5 to benzophenones and benzaldehydes is proposed based on deuterium-quenching experiments.
Spectrofluorimetric determination of trace nitrite with o-phenylenediamine enhanced by hydroxypropyl-β-cyclodextrin
Guo, Yu-Xian,Zhang, Qing-Feng,Shangguang, Xincheng,Zhen, Guodong
, p. 107 - 111 (2013)
A simple and sensitive spectrofluorimetric method was developed for the determination of nitrite in environmental and food samples. The method was based on the selective reaction of o-phenylenediamine with nitrite in acidic medium to form benzotriazole, which exhibited strong fluorescence at 568 nm with excitation at 420 nm in alkaline medium. The detection limit and sensitivity of the proposed method were improved by hydroxypropyl-β-cyclodextrin through complexation. The linear calibration range for nitrite was 0.04-0.8 μg mL-1 with a detection limit of 13.6 ng mL-1 (S/N = 3.29). The relative standard deviation for ten determinations of 0.1 and 0.4 μg mL-1 nitrite were 1.38% and 2.01%, respectively. Twenty-eight coexistent ions were examined, and no serious interference for most of ions was observed. The proposed method was successfully applied for the determination of nitrite in the water, sausage and soil samples with recoveries of 95.5-108.5%. The results were in good agreement with the recommended AOAC method.
Release of nitrosating species in the course of reduction of benzo-1,2,3,4-tetrazine 1,3-dioxides.
Ratnikov, Maxim O,Lipilin, Dmitry L,Churakov, Aleksandr M,Strelenko, Yuri A,Tartakovsky, Vladimir A
, p. 3227 - 3229 (2002)
[reaction: see text] The reduction of benzo-1,2,3,4-tetrazine 1,3-dioxides (BTDOs) 1 with Na(2)S(2)O(4) or SnCl(2) is suggested to proceed via intermediate N-nitrosobenzotriazoles 3 to afford benzotriazoles 2. The (15)N-labeling experiments exhibit that t
Expedient synthesis and anticancer evaluation of dual-action 9-anilinoacridine methyl triazene chimeras
Walunj, Dipak,Egarmina, Katarina,Tuchinsky, Helena,Shpilberg, Ofer,Hershkovitz-Rokah, Oshrat,Grynszpan, Flavio,Gellerman, Gary
, p. 237 - 252 (2020/08/21)
The efficient synthesis of molecular hybrids including a DNA-intercalating 9-anilinoacridine (9-AnA) core and a methyl triazene DNA-methylating moiety is described. Nucleophilic aromatic substitution (SNAr) and electrophilic aromatic substitution (EAS) reactions using readily accessible starting materials provide a quick entry to novel bifunctional anticancer molecules. The chimeras were evaluated for their anticancer activity. Chimera 7b presented the highest antitumor activity at low micromolar IC50 values in antiproliferative assays performed with various cancer cell lines. In comparison, compound 7b outperformed DNA-intercalating drugs like amsacrine and AHMA. Mechanistic studies of chimera 7b suggest a dual mechanism of action: methylation of the DNA-repairing protein MGMT associated with the triazene structural portion and Topo II inhibition by intercalation of the acridine core.
N-Aroylbenzotriazoles as Efficient Reagents for o-Aroylation in Absence of Organic Solvent
Hahnvajanawong, Viwat,Phungpis, Baramee
, p. 2671 - 2674 (2021/10/25)
N-Aroylbenzotriazoles have been shown to be efficient reagents for esterification in the absence of organic solvent. Grinding of N-aroylbenzoytiazoles with twofold excess of alcohols for a couple of hours at room temperature gave corresponding esters in high percentage of yields.
Method for synthesizing benzotriazole by one-step method
-
Paragraph 0018-0025, (2020/05/30)
The invention belongs to the technical field of fine chemical synthesis, and provides a method for synthesizing benzotriazole by a one-step method. The method comprises: carrying out diazotization andcyclization one-step synthesis on o-phenylenediamine, glacial acetic acid and sodium nitrite, crystallizing, washing water, and drying to obtain benzotriazole. The method overcomes the problems of harsh reaction conditions and low yield.
A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides
Sun, Wanwan,Chen, Xiaobei,Hu, Ying,Geng, Huihui,Jiang, Yuanrui,Zhou, Yuxin,Zhu, Wenjing,Hu, Min,Hu, Haohua,Wang, Xingyi,Wang, Xinli,Zhang, Shilei,Hu, Yanwei
supporting information, (2020/10/05)
A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.
Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
Heredia, Micaela D.,Guerra, Walter D.,Barolo, Silvia M.,Fornasier, Santiago J.,Rossi, Roberto A.,Budén, Mariá E.
supporting information, p. 13481 - 13494 (2020/12/15)
Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.
