95-14-7Relevant articles and documents
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.
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.
Method for synthesizing benzotriazole by one-step method
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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.
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
, (2020/07/13)
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.
tert-Butyl nitrite catalyzed synthesis of benzimidazoles from o-phenylenediamine and aldehydes at room temperature
Azeez, Sadaf,Chaudhary, Priyanka,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Sureshbabu, Popuri
, (2020/02/22)
A simple and efficient method is demonstrated for the synthesis of benzimidazoles via cyclocondensation of o-phenylenediamine with aldehydes in the presence of catalytic amount of tert-butyl nitrite. All the reactions were carried out at room temperature while the desired products were obtained in good to excellent yields.
Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine
Korvinson, Kirill A.,Akula, Hari K.,Malinchak, Casina T.,Sebastian, Dellamol,Wei, Wei,Khandaker, Tashrique A.,Andrzejewska, Magdalena R.,Zajc, Barbara,Lakshman, Mahesh K.
supporting information, p. 166 - 176 (2020/01/02)
Facile reduction of aryl halides with a combination of 5% Pd/C, B2(OH)4, and 4-methylmorpholine is reported. Aryl bromides, iodides, and chlorides were efficiently reduced. Aryl dihalides containing two different halogen atoms underwent selective reduction: I over Br and Cl, and Br over Cl. Beyond these, aryl triflates were efficiently reduced. This combination was broadly general, effectuating reductions of benzylic halides and ethers, alkenes, alkynes, aldehydes, and azides, as well as for N-Cbz deprotection. A cyano group was unaffected, but a nitro group and a ketone underwent reduction to a low extent. When B2(OD)4 was used for aryl halide reduction, a significant amount of deuteriation occurred. However, H atom incorporation competed and increased in slower reactions. 4-Methylmorpholine was identified as a possible source of H atoms in this, but a combination of only 4-methylmorpholine and Pd/C did not result in reduction. Hydrogen gas has been observed to form with this reagent combination. Experiments aimed at understanding the chemistry led to the proposal of a plausible mechanism and to the identification of N,N-bis(methyl-d3)pyridin-4-amine (DMAP-d6) and B2(OD)4 as an effective combination for full aromatic deuteriation. (Figure presented.).
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.
Method and device for continuous post-processing of benzotriazole synthetic fluid
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Paragraph 0023; 0032-0034, (2019/08/06)
The invention belongs to the technical field of petrochemical engineering, relates to a method for continuous post-processing of benzotriazole (BTA for short) synthetic fluid, and more specifically, relates to a method for synthesizing BTA through performing continuous post-processing steps such as acidification, washing, extraction, back extraction, dehydration and distillation on the BTA synthetic fluid. According to the method for continuous post-processing of the benzotriazole synthetic fluid, extraction separation is realized by utilizing the difference of solubility of the BTA in water under different PH (Potential of Hydrogen); a large quantity of evaporation energy does not need to be consumed; operation is simple; environmental pollution is little; the economical efficiency is strong; energy consumption is low, and industrialization is easy to realize.
Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines
Faggyas, Réka J.,Sloan, Nikki L.,Buijs, Ned,Sutherland, Andrew
, p. 5344 - 5353 (2019/05/21)
An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.
