344-62-7Relevant academic research and scientific papers
First aromatic ring acetamidation by anodic oxidation
Barba, Fructuoso,Barba, Isidoro,Batanero, Belen
, p. 115 - 117 (2014)
Anodic oxidation of 1-(trifluoromethyl)benzene in dry acetonitrile/Bu4NBF4under constant potential conditions led to 2-(trifluoromethyl) acetanilide in 86% yield. Other experimental conditions, as the use of constant current or the c
Acetonitrile and benzonitrile as versatile amino sources in copper-catalyzed mild electrochemical C-H amidation reactions
Budnikova, Yulia,Kononov, Alexander,Rizvanov, Ildar,Strekalova, Sofia
, p. 37540 - 37543 (2021/12/07)
A mild, efficient electrochemical approach to the site-selective direct C-H amidation of benzene and its derivatives with acetonitrile and benzonitrile has been developed. It has been shown that joint electrochemical oxidation of various arenes in the presence of a copper salt as a catalyst and nitriles leads to the formation of N-phenylacetamide from benzene and N-benzylacetamides from benzyl derivatives (up to 78% yield). A favorable feature of the process is mild conditions (room temperature, ambient pressure, no strong oxidants) that meet the criteria of green chemistry.
Visible-light-induced Pd-catalyzed: Ortho -trifluoromethylation of acetanilides with CF3SO2Na under ambient conditions in the absence of an external photocatalyst
Zou, Long,Li, Pinhua,Wang, Bin,Wang, Lei
supporting information, p. 3737 - 3740 (2019/04/01)
A visible-light-induced Pd-catalyzed ortho-trifluoromethylation of acetanilides with CF3SO2Na was developed. The reaction proceeded smoothly at room temperature in air without any external photocatalyst or additive, providing the desired products in moderate to good yields with good functional group tolerance and regioselectivity.
Visible-Light Mediated ortho-Trifluoromethylation of Aniline Derivatives
Tian, Chao,Wang, Qiyue,Wang, Xueqi,An, Guanghui,Li, Guangming
, p. 14241 - 14247 (2019/10/16)
A general visible-light mediated ortho-C-H trifluoromethylation of aniline derivatives by using a low-cost and stable Langlois reagent (CF3SO2Na) as the "CF3" source has been developed. In contrast to previous reports, this strategy allowed access to elusive trifluoromethyl lactams. Furthermore, mechanism experiments revealed that a copper/photoredox dual catalytic mechanism enabled general trifluoromethylation of aniline derivatives.
Fungicidal Properties of Some Novel Trifluoromethylphenyl Amides
Tsikolia, Maia,Bernier, Ulrich R.,Wedge, David E.,Tabanca, Nurhayat,Abboud, Khalil A.,Linthicum, Kenneth J.
, (2019/05/10)
Trifluoromethylphenyl amides (TFMPAs) were designed and synthesized as potential pesticides. Thirty-three structures were evaluated for fungicidal activity against three Colletotrichum species using direct bioautography assays. Active compounds were subsequently tested against C. fragariae, C. gloeosporioides, C. acutatum, Phomopsis obscurans, P. viticola, Botrytis cinerea and Fusarium oxysporum. The study identified 2-chloro-N-[2,6-dichloro-4-(trifluoromethyl)phenyl]acetamide (7a) as showing the strongest antifungal activity, and the broadest activity spectrum in this set against Colletotrichum acutatum (at 48 and 72 h) and Phomopsis viticola (at 144 h). The presence of triethylamine in its complex with N-[2,6-dichloro-4-(trifluoromethyl)phenyl]-2,2,3,3,3-pentafluoropropanamide (7b′) played an important role in the bioactivity, and depending on the concentration or fungal species it showed higher or lower activity than the parent amide. X-Ray crystallography has shown that the complex (7b′) is an ion pair, (C10H2Cl2F8NO)? (C6H16N)+, where a proton is transferred from the amide nitrogen to the triethylamine nitrogen and then connected by hydrogen bonding to the acyl oxygen (N?H 0.893 ?; H???O 1.850 ?; N???O 2.711 ?; N?H???O 161.2(13)°). Although none of these compounds were better than standards, this work revealed some potential lead structures for further development of active novel compounds.
Acetanilide and bromoacetyl-lysine derivatives as activators for human histone deacetylase 8
Mukhtar, Yusif M.,Huang, Yajun,Liu, Jiajia,Chen, Di,Zheng, Weiping
supporting information, p. 2319 - 2323 (2017/05/09)
In the current study, seven compounds (i.e. 1–7) were found to be novel activators for the Nε-acetyl-lysine deacetylation reaction catalyzed by human histone deacetylase 8 (HDAC8). When assessed with the commercially available HDAC8 peptide substrate Fluor-de-Lys-HDAC8 that harbors the unnatural 7-amino-4-methylcoumarin (AMC) residue immediately C-terminal to the Nε-acetyl-lysine residue to be deacetylated, our compounds exhibited comparable activation potency to that of TM-2-51, the strongest HDAC8 activator reported in the current literature. However, when assessed with an AMC-less peptide substrate derived from the native HDAC8 non-histone substrate protein Zinc finger protein ZNF318, while our compounds were all found to be able to activate HDAC8 deacetylation reaction, TM-2-51 was found not to be able to. Our compounds also seemed to be largely selective for HDAC8 over other classical HDACs. Moreover, treatment with the strongest activator among our compounds (i.e. 7) was found to decrease the KM of the above AMC-less HDAC8 substrate, while nearly maintaining the kcat of the HDAC8-catalyzed deacetylation on this substrate.
2-fluoro-6-trifluoromethylbenzenesulfonyl chloride synthesis method
-
Paragraph 0035-0036; 0050-0052, (2017/08/30)
The present invention provides a 2-fluoro-6-trifluoromethylbenzenesulfonyl chloride synthesis method. According to the reaction formula defined in the specification, o-trifluoromethylaniline is used as a raw material, and acylation, alkylation, nitration, dealkylation, reduction, diazotization fluorination, hydrolysis and sulfonylation are performed to synthesize an intermediate 2-fluoro-6-trifluoromethylbenzenesulfonyl chloride. According to the present invention, the target is that the synthesis process is suitable for the industrial production, the starting raw material is easy to obtain, the raw material cost is low, the process operating condition is mild, and the method is suitable for industrial production.
Quantitative insights into energy contributions of intermolecular interactions in fluorine and trifluoromethyl substituted isomeric N-phenylacetamides and N-methylbenzamides
Panini, Piyush,Chopra, Deepak
, p. 3711 - 3733 (2013/07/26)
The presence of the C-F bond in organic molecules, particularly in the context of generating different intermolecular interactions of the type C-F...F-C, C-H...F and C-F...π is of extreme significance in the realm of structural chemistry. These interactions generate different packing motifs in the formation of the crystal. It is of interest to evaluate the energetic contributions of such weak interactions to evaluate their important role in crystal packing. In this respect, a library of twelve compounds containing a strong donor and acceptor, along with the presence of a C-F bond in different electronic environments (fluorine atom connected to C(sp2) and C(sp3) carbon atom) have been synthesized and characterized using single crystal X-ray diffraction studies at low temperature. In addition, the non-fluorinated counterpart has also been synthesized. These crystal structures have been analyzed to understand the contribution of weak interactions involving organic fluorine in the crystal packing. Furthermore, the stabilizing-destabilizing roles of such interactions in terms of favourable energetics have been quantified with inputs from calculations performed using PIXEL. It is observed that most of the interactions involving fluorine are of a dispersive character, and in some cases the interaction is also coulombic in origin. These results have been compared with ab initio quantum-chemical calculations (DFT-D3/B-97D level) performed using TURBOMOLE. In addition, the lattice energies of all the compounds have been evaluated, and the total contribution partitioned into the corresponding coulombic, polarization, dispersion and exchange contributions using the CLP module. The results correlate well with thermochemical data experimentally determined for these compounds.
Lewis basic ionic liquid as an efficient and facile catalyst for acetylation of alcohols, phenols, and amines under solvent-free conditions
Ji, Li,Qian, Chao,Chen, Xin-Zhi
, p. 369 - 374 (2013/05/21)
The Lewis basic ionic liquid 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate was employed for the acetylation of various phenols, alcohols, and amines in good-to-excellent yields at 50 C under solvent-free conditions in a short time. Compared with existing methods based on conventional catalysts and toxic solvents, the reported method is simple, mild and environmentally viable. Furthermore, the ionic liquid was conveniently separated from the products and easily recycled to catalyze other acetylation reactions with excellent yields. .
Silver-catalysed trifluoromethylation of arenes at room temperature
Seo, Sangwon,Taylor, John B.,Greaney, Michael F.
supporting information, p. 6385 - 6387 (2013/08/23)
A variety of heteroarenes and electron rich arenes can be trifluoromethylated at room temperature with TMSCF3, catalytic silver and PhI(OAc)2.
