- Regioselective synthesis of 2-acetyl- and 2-alkoxycarbonyl-3- (trifluoromethyl)phenols by [3+3] cyclization of 1,3-bis-silyl enol ethers with 4-ethoxy- and 4-silyloxy-1,1,1-trifluoroalk-3-en-2-ones
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2-Acetyl- and 2-alkoxycarbonyl-3-(trifluoromethyl)phenols were prepared by [3+3] cyclization of 1,3-bis-silyl enol ethers with 4-ethoxy- and 4-silyloxy-1,1,1-trifluoroalk-3-en-2-ones.
- Mamat, Constantin,Pundt, Thomas,Schmidt, Andreas,Langer, Peter
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Read Online
- New air-stable uranium(IV) complexes with enhanced volatility
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Herein we report the synthesis and characterization of new air-stable uranium(iv) complexes based on three different heteroarylalkenolate ligands namely DMOPFB (1) (1-(4,5-dimethyl-oxazol-2-yl)-3,3,4,4,4-pentafluoro-but-1-en-2-ol) with an elongated fluori
- Leduc, Jennifer,Ravithas, Rajitha,Rathgeber, Lisa,Mathur, Sanjay
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Read Online
- Fluorinated Cerium(IV) Enaminolates: Alternative Precursors for Chemical Vapor Deposition of CeO2 Thin Films
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High-yield synthesis of four new fluorinated enaminones LH2 (RfC(O)C2H2NH)2C2H4 (Rf = CF3 (2a), C2F5 (2b), C3F7 (2c)) and (F3CC(O)C2H2NH)2C3H6 (2a′) as dianionic ligands is described. The ligands were characterized in solution (via nuclear magnetic resoannce (NMR)) as well as in the solid state (via X-ray diffraction (XRD)). The ligating ability of the enaminones was verified by reacting them with [Ce2(OiPr)8(HOiPr)2], which resulted in monomeric cerium(IV) complexes [CeL2] (3a-c, 3a′) based on tetradentate chelation of the ligands. Cerium enaminolates were comprehensively analyzed by NMR spectroscopy, mass spectrometry, and single-crystal XRD studies to verify their monomeric nature. High stability under ambient conditions and high volatility makes them a potential precursor for the gas-phase synthesis of CeO2. Complexes 3a and 3b were applied as precursors in thermal and plasma-enhanced chemical vapor deposition to obtain crystalline ceria films with different surface morphologies. The purity and surface states of the films were analyzed by X-ray photoelectron spectroscopy, which revealed a high amount of Ce3+ on the subsurface of CeO2 films.
- Schl?fer,Graf,Fornalczyk,Mettenb?rger,Mathur
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Read Online
- 2-(Halogenated Phenyl) acetamides and propanamides as potent TRPV1 antagonists
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A series consisting of 117 2-(halogenated phenyl) acetamide and propanamide analogs were investigated as TRPV1 antagonists. The structure–activity analysis targeting their three pharmacophoric regions indicated that halogenated phenyl A-region analogs exhibited a broad functional profile ranging from agonism to antagonism. Among the compounds, antagonists 28 and 92 exhibited potent antagonism toward capsaicin for hTRPV1 with Ki[CAP] = 2.6 and 6.9 nM, respectively. Further, antagonist 92 displayed promising analgesic activity in vivo in both phases of the formalin mouse pain model. A molecular modeling study of 92 indicated that the two fluoro groups in the A-region made hydrophobic interactions with the receptor.
- Ann, Jihyae,Bahrenberg, Gregor,Blumberg, Peter M.,Choi, Sun,Christoph, Thomas,Do, Nayeon,Frank-Foltyn, Robert,Ha, Heejin,Jeong, Jin Ju,Kang, Jin Mi,Kim, Changhoon,Kwon, Sun Ok,Lee, Jeewoo,Lee, Sunho,Lesch, Bernhard,Stockhausen, Hannelore,Vu, Thi Ngoc Lan,Yoon, Sanghee
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- Continuous preparation method of trifluoromethyl butenone derivative
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The invention discloses a continuous preparation method of a trifluoromethyl butenone derivative. The continuous preparation method is characterized in that a raw material 1 as shown in a structure (I) in a reaction formula and trifluoroacetyl halide serving as a raw material 2 react in a microchannel reactor to prepare the trifluoromethyl butenone derivative as shown in a structure (II). The structure (I) and the structure (II) are as described in the specification. In the structure (I) and the structure (II), R is an electron donating group and can be conjugated with olefin double bonds; R1 and R2 are independently selected from hydrogen, C1-C20 alkyl groups, aryl groups, and substituted aryl groups or silyl groups; and X is halogen and is selected from fluorine, chlorine, bromine and iodine. The method has the advantages of good process universality, good atom economy, high yield, few byproducts, high product purity and the like.
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Paragraph 0035-0036
(2021/06/22)
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- Preparation method of N-(2-methoxycarbonyl vinyl)-4, 4, 4-trifluoro-3-ketone-1-buteneamine
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The invention belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of N-(2-methoxycarbonyl vinyl)-4, 4, 4-trifluoro-3-ketone-1-buteneamine, and the preparation method of N-(2-methoxycarbonyl vinyl)-4, 4, 4-trifluoro-3-ketone-1-buteneamine comprises the following steps: taking trifluoroacetic acid, vinyl ethyl ether, methylsulfonyl chloride and pyridine as raw materials, firstly preparing 4-ethoxy-1, 1, 1-trifluoro-3-butene-2-ketone, carrying out ammonia ammoniation to obtain 4-amino-1, 1, 1-trifluoro-3-butene-2-ketone, then, under the action of sodium hydroxide, reacting with methyl 3-methoxyacrylate to obtain a target product N-(2-methoxycarbonyl vinyl)-4, 4, 4-trifluoro-3-ketone-1-buteneamine. The adopted raw materials are relatively cheap and easy to obtain, and the method is easy and convenient to operate, safe, feasible, high in cost performance and suitable for industrial production.
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Paragraph 0017; 0020; 0023; 0026; 0029; 0032; 0035; 0038
(2021/07/17)
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- Preparation process 4 - trifluoromethyl nicotinic acid
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The invention discloses a preparation process of 4 -trifluoromethyl nicotinic acid and vinyl ether. Trifluoracetyl chloride and catalyst were added to the reactor and stirred. Acylation to obtain 4 - ethoxy -1, 1, 1 -trifluoro -3 - alkene -2 - ketone, reacting 4 - with a catalyst and an oxidizing agent to -1 ethoxy 1, 1 -3 -trifluoro -2 -butenone, 25 - 90 °C g 30 - 60min of 1-trifluoroethyl 1-butenecone, adding 1 - equivalents of alkali lye, and then acidifying to obtain -4 - 2-trifluoromethylnicotiniconicotinic acid, followed by acidification with -3 - 4 -chloro 1 - 5-4 - trifluoromethyl POCl3 picolinic 6 - acid -4 . The preparation method of 4 -trifluoromethyl nicotinic acid is optimized. Only the reaction temperature is controlled, the intermediate product can be used for subsequent reaction steps, the reaction requirements in the step process are reduced, the requirement for equipment is low, and industrialization can be conveniently realized.
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Paragraph 0021-0022; 0027-0028; 0033-0034; 0039-0040
(2021/10/11)
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- KRAS G12C Mutant protein inhibitor and pharmaceutical composition thereof Preparation method and application
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The present invention provides compounds having irreversible inhibitor activity G12C mutant KRAS protein, racemates, stereoisomers, pharmaceutically acceptable salts, polymorphs or solvates thereof, the structure of which is shown in formula (I). Also provided are methods related to the preparation and use of such compounds, pharmaceutical compositions comprising such compounds, and methods of modulating G12C mutant KRAS protein activity for treatment of disorders such as cancer.
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Paragraph 0191; 0193; 0197-0199
(2021/10/27)
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- Continuous synthesis method of 4-ethoxy-1, 1, 1-trifluoro-3-butene-2-one
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The invention provides a continuous synthesis method of 4-ethoxy-1, 1, 1-trifluoro-3-butene-2-one. The continuous synthesis method comprises the following steps: enabling raw materials containing vinyl ethyl ether, triethylamine and trifluoroacetic anhydride to continuously enter a continuous reactor to react so as to obtain a product system containing the 4-ethoxy-1, 1, 1-trifluoro-3-butene-2-one; performing continuous extraction on the product system to obtain the 4-ethoxy-1, 1, 1-trifluoro-3-butene-2-one, and performing continuous extraction on the product system to obtain the 4-ethoxy-1, 1, 1-trifluoro-3-butene-2-one. By using a continuous process, the raw materials can be conveniently and accurately pumped into the continuous reactor, and after the reaction is finished, continuous extraction is also used for post-treatment, so that the whole process is quick, simple and efficient, the efficiency of the whole synthesis process is greatly improved, and the damage loss of a product is reduced; and the potential safety hazard of batch production is avoided. After amplification, an amplification effect does not exist, and safety and high synthesis efficiency can still be kept.
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Paragraph 0040-0077
(2020/05/08)
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- Nanostructured IrOx Coatings for Efficient Oxygen Evolution Reactions in PV-EC Setup
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New heteroleptic iridium compounds exhibiting high volatility and defined thermal decomposition behavior were developed and tested in plasma-enhanced chemical vapor deposition (PECVD). The iridium precursor [(COD)Ir(TFB-TFEA)] (COD = 1,5-cyclooctadiene; TFB-TFEA = N-(4,4,4-Trifluorobut-1-en-3-on)-6,6,6-trifluoroethylamin) unifies both reactivity and sufficient stability through its heteroleptic constitution to offer a step-by-step elimination of ligands to provide high compositional purity in CVD deposits. The substitution of neutral COD ligands against CO groups further increased the volatility of the precursor. PECVD experiments with unambiguously characterized Ir compounds (single crystal X-ray diffraction analysis) demonstrated their suitability for an atom-efficient (high molecule-to-precursor yield) gas phase deposition of amorphous iridium oxide (IrOx) phases. Thin films of IrOx were well suited as electrocatalyst in oxygen evolution reaction so that an efficient coupled system in combination with solar cells is viable to perform water-splitting reaction without external bias.
- Jürgensen, Lasse,Frank, Michael,Graf, David,Gessner, Isabel,Fischer, Thomas,Welter, Katharina,J?germann, Wolfram,Mathur, Sanjay
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p. 911 - 924
(2020/03/19)
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- Controlled growth of Cu and CuOxthin films from subvalent copper precursors
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A new Cu(i) precursor, [(COD)Cu(TFB-TFEA)] (COD = 1,5-cyclooctadiene and TFB-TFEA =N-(4,4,4-trifluorobut-1-en-3-on)-6,6,6-trifluoroethylamine) with high volatility and a clean thermal decomposition pattern was tested for thermal and plasma-assisted chemical vapor deposition (CVD). The heteroleptic configuration based on an anionic and a chelating neutral ligand unified both reactivity and sufficient stability resulting in an intrinsic molecular control over the composition of the resulting CVD deposits. The electronic influence of the ligand on the metal site was studied by 1D and 2D NMR spectroscopy, while EI mass spectrometry revealed the ligand elimination cascade. Thermal and plasma CVD experiments demonstrated the suitability of the copper compound for an atom-efficient (high molecule-to-material yield) deposition of copper(0) and copper(i) oxide films that could be converted into crystalline copper(ii) oxide upon heat treatment at 500 °C.
- Jürgensen, Lasse,H?ll, David,Frank, Michael,Ludwig, Tim,Graf, David,Schmidt-Verma, Anna Katrin,Raauf, Aida,Gessner, Isabel,Mathur, Sanjay
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p. 13317 - 13325
(2020/10/13)
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- Discovery of cyanopyridine scaffold as novel indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors through virtual screening and preliminary hit optimisation
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With the aim of discovering novel IDO1 inhibitors, a combined similarity search and molecular docking approach was employed to the discovery of 32 hit compounds. Testing the screened hit compounds has led to several novel submicromolar inhibitors. Especially for compounds LVS-019 with cyanopyridine scaffold, showed good IDO1 inhibitory activity. To discover more compounds with similar structures to LVS-019, a shape-based model was then generated on the basis of it and the second-round virtual screening was carried out leading to 23 derivatives. Molecular docking studies suggested a possible binding mode of LVS-019, which provides a good starting point for the development of cyanopyridine scaffold compounds as potent IDO1 inhibitor. To improve potency of these hits, we further designed and synthesised another 14 derivatives of LVS-019. Among these compounds, LBJ-10 showed improved potency compared to the hits and displayed comparable potency to the control GDC-0919 analogue. LBJ-10 can serve as ideal leads for further modifications as IDO1 inhibitors for cancer treatment.
- Xu, Xi,Ren, Jie,Ma, Yinghe,Liu, Hongting,Rong, Quanjin,Feng, Yifan,Wang, Yameng,Cheng, Yu,Ge, Ruijia,Li, Zhiyu,Bian, Jinlei
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p. 250 - 263
(2019/01/10)
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- A chromium picolinate food additive novel preparation method of
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The invention discloses a novel preparation method of a chromium picolinate type food additive, and belongs to the technical field of synthesis of a food additive. The chromium picolinate type food additive adopts the following structure as shown in the description. The invention further discloses a preparation method of the chromium picolinate type food additive. The chromium picolinate type food additive is synthetized by a new method, the reaction process is simple and easy to operate, the raw materials are cheap and easy to obtain, the reaction efficiency is high, the repeatability is good, and the chromium picolinate type food additive has favorable growth effect on growing fattening pigs, and has low biological accumulation properties.
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Paragraph 0024-0026
(2019/10/23)
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- Synthetic method for 6-trifluoromethyl-nicotinic acid
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The invention discloses a method for synthesizing 6-trifluoromethyl-nicotinic acid. The method comprises the specific steps: carrying out addition-elimination reaction reactions on trifluoroacetic acid and vinyl ethyl ether under the action of phosphorus pentachloride to obtain 4-ethoxyl-1,1,1-trifluoro-3-butene-2-one; carrying out addition-elimination reaction reactions on ethidene diamine and cyanoacetic acid in a heating condition to obtain 3-(diethyl amino) acrylonitrile first; carrying out an Stork alkylation reaction on 3-(diethyl amino) acrylonitrile and 4-ethoxyl-1,1,1-trifluoro-3-butene-2-one to obtain 2-((diethyl amino) methylene)-6,6,6-trifluoro-5-oxo-3-hexenenitrile; carrying out exocondensation on 2-((diethyl amino) methylene)-6,6,6-trifluoro-5-oxo-3-hexenenitrile under the action of ammonium acetate to obtain 6-trifluoromethyl cyanopyridine; and carrying out cyano hydrolysis reaction on the 6-trifluoromethyl cyanopyridine t obtain 6-trifluoromethyl-nicotinic acid. The synthetic method is more economic, environmentally friendly, efficient and simple.
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Paragraph 0016-0025
(2019/01/17)
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- Method for preparing 4-(trifluoromethyl)nicotinic acid
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The invention discloses a method for preparing 4-(trifluoromethyl)nicotinic acid, and belongs to the technical field of methods for preparing chemical pharmaceutical intermediates. The method comprises steps of using trifluoroacetyl chloride, vinyl ethyl ether and 3-aminoacrylonitrile as raw materials to prepare the 4-(trifluoromethyl)nicotinic acid through acylation, cyclization and hydrolysis reactions. The method provided by the invention is relatively cheap and easily available in adopted raw material, simple and convenient to operate, easy in separation and purification of products in each step, high in yield, and more suitable for industrial production.
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Paragraph 0022-0027
(2019/03/29)
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- Volatile Rhenium(I) Compounds with Re-N Bonds and Their Conversion into Oriented Rhenium Nitride Films by Magnetic Field-Assisted Vapor Phase Deposition
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New heteroleptic rhenium(I) compounds, [fac-Re(I)(CO)3(L)] (e.g., L= tfb-dmpda, (N,N-(4,4,4-T.
- Frank, Michael,Jürgensen, Lasse,Leduc, Jennifer,Stadler, Daniel,Graf, David,Gessner, Isabel,Zajusch, Fabian,Fischer, Thomas,Rose, Marc-André,Mueller, David N.,Mathur, Sanjay
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p. 10408 - 10416
(2019/09/07)
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- One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones
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A one-pot transformation of α,β-unsaturated trifluoromethyl ketones with 2-(phenylsulfinyl)acetamide to give trifluoromethylated 2-pyridones is realized. The reaction proceeds under mild conditions and involves multiple steps in an expeditious and controlled sequence to provide efficient access to a broad range of trifluoromethylated 2-pyridones in moderate to high yields. Moreover, further synthetic manipulations permit the routine synthesis of a diverse array of trifluoromethylated pyridines with good efficiency.
- Lv, Ning,Tian, Yi-Qiang,Zhang, Fa-Guang,Ma, Jun-An
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supporting information
p. 605 - 609
(2019/03/07)
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- Method for preparing heterocyclic small molecule compound
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The invention belongs to the field of medical chemistry, particularly belongs to the field of organic synthesis in medical chemistry, and more particularly relates to a preparation method of a heterocyclic small molecule compound. According to the preparation method, vinyl ethyl ether is used as a raw material, and a target compound, trifluoromethylpyrazole borate, is obtained through four steps.The product is an important building block in drug research, development and synthesis, and the industrial preparation method of the product can provide guarantee for subsequent in-depth research anddevelopment. Therefore, the invention is beneficial to research and development of related drug synthesis.
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Paragraph 0047; 0048; 0055; 0056
(2019/10/01)
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- A fluorine-containing oxazolidinone compounds and its preparation method and application
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The invention discloses a fluorine-containingoxazolidinonecompound as well as a preparation method and an application thereof. The structural formula of the fluorine-containingoxazolidinonecompound is as follows, wherein Rf refers to a trifluoromethyl group, a difluoromethyl group, a fluorine atom or perfluoralkane, R and Rindependently refer to H, C1-C6 straight-chain or branchedalkyl groups, C1-C6 straight-chain or branchedperfluoroalkyl groups, C1-C6 straight-chain or branchedalkoxygroups, a halogen such as F, Cl, Br or I, a nitro group, a cyano group or a phenyl group; R, R, R and Rindependently refer to H, F, Cl, Br, I or C1-C3 alkyl groups. The fluorine-containingoxazolidinonecompound has the better antimicrobial activity on watermelonanthracnose and cucumber grey mold and is particularly good in inhibitory activity on phytopathogencucumber grey mold of imperfect fungihyphomycetes, and a new choice is provided for development and utilization of new sterilization pesticides.
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Paragraph 0036; 0037; 0038; 0079; 0080; 0081; 0082-0086
(2017/08/25)
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- Substituted amide compound and application
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The invention belongs to the field of agricultural bactericidal, insecticidal and acaricidal agents, and relates to a substituted amide compound and an application. The substituted amide compound has a structure as shown in a general formula I in the specification; and in the general formula I, substituents are defined in the specification. The compound provided by the invention has broad-spectrum bactericidal, insecticidal and acaricidal activities, has excellent control effects on diseases like cucumber downy mildew, corn rust, wheat powdery mildew and rice blast, especially has better control effects on the corn rust, also has excellent control effects on aphids and Tetranychus cinnabarinus, and especially can obtain good effects on the Tetranychus cinnabarinus at a low dosage.
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Paragraph 0165-0168
(2017/06/27)
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- Substituted tetrahydroisoquinoline compound and application
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The invention discloses a substituted tetrahydroisoquinoline compound and application. The compound has a structure as shown in a general formula I in the specification; and in the general formula I, substituents are defined in the specification. The comp
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Paragraph 0198; 0199; 0200
(2017/07/23)
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- Preparation method and application of oxazoles compound with immunosuppressive activity
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The invention discloses a preparation method and application of an oxazoles compound with immunosuppressive activity, and belongs to the technical field of medicine synthesis. The key point of the technical scheme is that the oxazoles compound with the immunosuppressive activity has the following structure as shown in the specification. The invention further discloses the preparation method of the oxazoles compound with the immunosuppressive activity. The oxazoles compound with the immunosuppressive activity is synthesized through a novel method; the reaction process is simple and feasible; raw materials are low in cost and readily available; the reaction efficiency and the repetitiveness are relatively high; and the immunosuppressive activity effect is obvious.
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Paragraph 0027-0029
(2017/11/16)
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- Efficient synthesis method of chromium picolinate food additive
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The invention discloses an efficient synthesis method of a chromium picolinate food additive and belongs to the technical field of food additive synthesis. The chromium picolinate food additive has he following structure shown in the specification. The invention further discloses a preparation method of the chromium picolinate food additive. The chromium picolinate food additive is synthesized with a novel method, the reaction process is simple to operate and easy to implement, raw materials are easy to obtain, and the method is higher in reaction efficiency and better in repeatability, plays a good role in promoting growth of growing-finishing pigs and has very low bioaccumulation.
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Paragraph 0022; 0023; 0024
(2017/12/06)
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- Triazole compound with immunosuppression activity as well as preparation method and application thereof
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The invention discloses a triazole compound with immunosuppression activity as well as a preparation method and application thereof, and belongs to the technical field of medicine synthesis. According to the technical scheme of the invention, the triazole compound with immunosuppression activity is of a structure as shown in the specification. The invention further discloses a preparation method of the triazole compound with immunosuppression activity. The triazole compound with immunosuppression activity is synthesized by using a novel method, and is simple and feasible in operation in the reaction process, cheap and easy in raw material obtaining, relatively high in reaction velocity, relatively good in repeatability, and remarkable in immunosuppression activity.
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Paragraph 0027-0029
(2018/03/24)
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- Synthetic method of immunosuppressive medicine with oxazole ring
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The invention discloses a synthetic method of an immunosuppressive medicine with an oxazole ring and belongs to the technical field of medicine synthesis. The technical scheme has the key points that the immunosuppressive medicine with the oxazole ring has the following structure shown in the specification. The invention also discloses a preparation method of the immunosuppressive medicine with the oxazole ring. The synthetic method disclosed by the invention has the advantages that the immunosuppressive medicine is synthesized by a new method, the reaction process is simple and easy in operation, the materials are low in price and easy to obtain, the reaction efficiency is higher, the repeatability is better, and the Immunosuppressive-activity effect is obvious.
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Paragraph 0021; 0027-0029
(2018/03/01)
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- Having a three-nitrogen azoles ring structure of immunosuppressant drug synthesis method
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The invention discloses a has three nitrogen azoles ring structure of immunosuppressant drug synthesis method, which belongs to the technical field of medical synthesis. Technical proposal of the invention points are: having a three-nitrogen azoles ring structure immunosuppressive drug, has the following structure: The invention also discloses the has three nitrogen azoles ring structure of immunosuppressant drug preparation method. The invention through a new synthesis method with three nitrogen azoles ring structure the immunosuppressant drug, the reaction process is simple and easy operation, the raw material is cheap, relatively high reaction efficiency and good repeatability, the immunosuppressant drug active effect is obvious.
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Paragraph 0029; 0030; 0031
(2018/04/01)
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- 6-substituted pyrazolyl quinazolinone compound and use thereof
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The invention discloses a 6-substituted pyrazolyl quinazolinone compound which is represented by a formula I shown in the description or a salt of the compound represented by the formula I. The compound I represented by the formula I has excellent insecti
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Paragraph 0189; 0190; 0191
(2016/10/07)
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- Synthesizing method for 4-oxethyl-1,1,1-trifluoro-butene-2-ketone
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The invention relates to a synthesizing method for 4-oxethyl-1,1,1-trifluoro-butene-2-ketone. The method comprises the following steps that dichloromethane and pyridine are added in a reaction kettle, on the condition that the temperature is controlled at minus 10 DEG C-0 DEG C, trifluoroacetic acid is dropwise added, the dropwise adding time is controlled for 3-3.5 hours, and after dropwise adding is completed, stirring is performed for ten minutes; vinyl ethyl ether is added, on the condition that the temperature is controlled at minus 10 DEG C-0 DEG C, methylsulfonyl chloride is dropwise added, the dropwise adding time is controlled for 2 hours, after dropwise adding is completed, the temperature is slowly increased to 20 DEG C, and stirring is performed for staying overnight; filter pressing is performed on obtained products with a plate-and-frame filter press, and filter cakes are washed for two times with dichloromethane to collect pyridinium; normal-pressure desolventizing is performed on filtrate at 58 DEG C, the temperature is lowered to 20 DEG C to collect solvent, reduced-pressure distilling and desolventizing are performed at 58 DEG C to collect solvent to obtain crude products, reduced-pressure rectifying is performed on the crude products to collect overhead products, and the 4-oxethyl-1,1,1-trifluoro-butene-2-ketone is obtained. The synthesizing method for the 4-oxethyl-1,1,1-trifluoro-butene-2-ketone has the advantages of being simple and direct in technology, few in technology waste materials, high in yield and suitable for large-scale industrialized production.
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Paragraph 0009
(2016/10/17)
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- PROCESS FOR PREPARING HALOGENATED ALKENONE ETHERS AND THEIR USE IN THE SYNTHESIS OF ANTHRANILAMIDE PESTICIDES
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The present invention relates to a process for preparing a compound of formula (III) starting from the vinyl ether (IlIa) and the compound (IIIb) with a reagent (lllc) selected from the group of sulfonylhalides or sulfonylanhydrides, e.g. methanesulfonyl chloride or p-toluenesulfonyl chloride, in the presence of a base. The present invention relates also to processes comprising further preceding and/or subsequent reaction steps, leading to anthranilamide pesticides or to precursors for them.
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Page/Page column 24
(2016/06/01)
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- Electron-deficient heteroarenium salts: An organocatalytic tool for activation of hydrogen peroxide in oxidations
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A series of monosubstituted pyrimidinium and pyrazinium triflates and 3,5-disubstituted pyridinium triflates were prepared and tested as simple catalysts of oxidations with hydrogen peroxide, using sulfoxidation as a model reaction. Their catalytic efficiency strongly depends on the type of substituent and is remarkable for derivatives with an electron-withdrawing group, showing reactivity comparable to that of flavinium salts which are the prominent organocatalysts for oxygenations. Because of their high stability and good accessibility, 4-(trifluoromethyl)pyrimidinium and 3,5-dinitropyridinium triflates are the catalysts of choice and were shown to catalyze oxidation of aliphatic and aromatic sulfides to sulfoxides, giving quantitative conversions, high preparative yields and excellent chemoselectivity. The high efficiency of electron-poor heteroarenium salts is rationalized by their ability to readily form adducts with nucleophiles, as documented by low pKR+ values (pKR+ red > -0.5 V). Hydrogen peroxide adducts formed in situ during catalytic oxidation act as substrate oxidizing agents. The Gibbs free energies of oxygen transfer from these heterocyclic hydroperoxides to thioanisole, obtained by calculations at the B3LYP/6-311++g(d,p) level, showed that they are much stronger oxidizing agents than alkyl hydroperoxides and in some cases are almost comparable to derivatives of flavin hydroperoxide acting as oxidizing agents in monooxygenases.
- ?turala, Ji?í,Bohá?ová, Soňa,Chudoba, Josef,Metelková, Radka,Cibulka, Radek
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p. 2676 - 2699
(2015/03/18)
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- METHOD FOR PREPARATION OF 4-ALKOXY-1,1,1-TRIFLUOROBUT-3-EN-2- ONES FROM 1,1,1-TRIFLUOROACETONE
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The invention discloses a method for the preparation of 4-alkoxy-1,1,1-trifluorobut-3-en-2-ones from 1,1,1-trifluoroacetone.
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Page/Page column 8
(2016/01/12)
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- METHOD FOR PRODUCING ALKENONE ETHERS
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The present invention relates to a process for the synthesis of alkenone ethers.
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Page/Page column 7
(2015/02/19)
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- METHOD FOR PREPARATION OF 4-ALKOXY-1,1,1-TRIFLUOROBUT-3-EN-2-ONES FROM TRIFLUOROACETYLACETIC ACID
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The invention discloses a method for the preparation of 4-alkoxy and 4-aryloxy-1,1,1-trifluorobut-3-en-2-ones from trifluoroacetylacetic acid and orthoesters. Such compound can be used for the preparation of pharmaceutical, chemical or agro-chemical products.
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Page/Page column 15
(2015/02/02)
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- 6,6-Fused heterocyclic ureas as highly potent TRPV1 antagonists
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A series of N-[{2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)-pyridin-3-yl}methyl] N′-(6,6-fused heterocyclic) ureas have been investigated as hTRPV1 antagonists. Among them, compound 15 showed highly potent TRPV1 antagonism to capsaicin, with Ki(ant) = 0.2 nM, as well as antagonism to other activators, and it was efficacious in a pain model. A docking study of 15 with our hTRPV1 homology model indicates that there is crucial hydrogen bonding between the ring nitrogen and the receptor, contributing to its potency.
- Sun, Wei,Kim, Hyo-Shin,Lee, Sunho,Jung, Aeran,Kim, Sung-Eun,Ann, Jihyae,Yoon, Suyoung,Choi, Sun,Lee, Jin Hee,Blumberg, Peter M.,Frank-Foltyn, Robert,Bahrenberg, Gregor,Schiene, Klaus,Stockhausen, Hannelore,Christoph, Thomas,Frormann, Sven,Lee, Jeewoo
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p. 803 - 806
(2015/02/19)
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- Synthesis and in vitro antibacterial activity of novel fluoroalkyl-substituted pyrazolyl oxazolidinones
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A series of novel oxazolidinone derivatives bearing fluoroalkyl-substituted pyrazole as the C-ring structure were designed, synthesized and evaluated for their antibacterial activity against six Gram-positive bacterial pathogens. Most of the target compounds have good antibacterial activity. Especially, compounds 13f, 13i and 13l show excellent activity comparable to linezolid.
- Yan, Lili,Wu, Jingjing,Chen, Heng,Zhang, Shaowu,Wang, Zhi,Wang, Hui,Wu, Fanhong
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p. 73660 - 73669
(2015/09/15)
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- Synthesis and evaluation of original bioisosteres of bacterial type IIA topoisomerases inhibitors
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A recently discovered series of inhibitors of the ATPase function of bacterial type IIA topoisomerases featuring a carboxypyrrole component led us to attempt to replace this group with a potentially bioisosteric carboxypyrazole. Accordingly, synthetic pathways to 2-(4-(1H-pyrazole-5-carboxamido)piperidin-1-yl)thiazole-5-carboxylic acids or 2-(4-(N-methyl-1H-pyrazole-5-carboxamido)piperidin-1-yl)thiazole-5-carboxylic acids featuring an array of substituents on the pyrazole ring were explored. Unfortunately, none of the analogues made were effective on the ATPase function of Mycobacterium tuberculosis gyrase as well on the DNA supercoiling activity of the whole gyrase of M. tuberculosis and Escherichia coli. However, this work is still providing original insights in chemistry as well as in the structure-activity relationships of this series of inhibitors.
- Petrella, Stéphanie,Aubry, Alexandra,Janvier, Geneviève,Coutant, Eloi P.,Cartier, Alex,Dao, Thuy-Ha,Bonhomme, Frédéric J.,Motreff, Laurence,Pissis, Cédric,Bizet, Chantal,Clermont, Dominique,Begaud, Evelyne,Retailleau, Pascal,Munier-Lehmann, Hélène,Capton, Estelle,Mayer, Claudine,Janin, Yves L.
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p. 240 - 250
(2016/03/22)
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- The conformational analysis of push-pull enaminones using Fourier transform IR and NMR spectroscopy, and quantum chemical calculations. V. α-Methyl-, fluorine-β-N,N-dimethylaminovinyl trifluoromethyl ketones
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IR Fourier spectra of two enaminoketones with general formula F 3CCOCRCHN(CH3)2, R = F (DMTFBN); R = CH 3, (DMTMBN) were studied in various pure solvents. For comparison results of earlier investigated enaminoketone R = H (DMTBN) was also presented. On the basis of NMR and IR spectra it was shown that enaminoketones DMTBN, DMTFBN and DMTMBN presented in solutions as equilibrium of two conformers, (E-s-Z) (E-s-E) (for DMTFBN these conformers are denoted as (Z-s-Z) and (Z-s-E), respectively). DFT calculations were carried out to evaluate relative energy and dipole moment of each spatial form. It was shown that 'closed-ring' complex formation between (E-s-Z) and (E-s-E) conformers of DMTBN accounts for discrepancies between DFT calculations of conformer relative energies and experimentally evaluated enthalpies of (E-s-Z) (E-s-E) equilibrium. In α-substituted DMTFBN and DMTMBN, where formation of 'closed-ring' complex was impossible we did not observe such discrepancies. For both (E-s-Z) and (E-s-E) conformers of the DMTBN and DMTMBN the main influence on the ν (CO) vibrations has the solvent's hydrogen bond donor (HBD) acidity, whereas for the DMTFBN an influence of the solvent's polarity/polarizability dominated.
- Vdovenko, Sergey I.,Gerus, Igor I.,Zhuk, Yuri I.,Kukhar, Valery P.,R?schenthaler, Gerd-Volker
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- PROCESS FOR THE MANUFACTURE OF ALKENONES
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A process for the manufacture of an alkenone comprising the steps of: (a) providing a halogenated precursor of the alkenone and (b) subjecting at least a fraction of the halogenated precursor of step (a) to a thermolysis reaction to form a reaction mixture comprising the alkenone and a hydrogen halide wherein the hydrogen halide is removed from the reaction mixture by cyclonic separation is described.
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Page/Page column 7
(2014/03/25)
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- Neutral copper(i) dipyrrin complexes and their use as sensitizers in dye-sensitized solar cells
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Heteroleptic neutral copper(i) dipyrrin complexes have been synthesised with the general formula [Cu(4,4′-(R)-6,6′-(CH3)- bipyridine)(dipyrrin)], R = CH3 or CO2Et, and H-dipyrrin is either 1,3,7,9-tetramethyldipyrromethene
- Hewat, Tracy E.,Yellowlees, Lesley J.,Robertson, Neil
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supporting information
p. 4127 - 4136
(2014/03/21)
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- NOVEL TRIAZINE COMPOUNDS
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The present invention relates to novel triazine compounds of formula (1). The present invention also discloses compounds of formula I along with other pharmaceutical ac-ceptable excipients and use of the compounds to modulate the PI3K/ mTOR pathway
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Page/Page column 117
(2014/02/16)
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- A scalable and regioselective synthesis of 2-difluoromethyl pyridines from commodity chemicals
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A scalable de novo synthesis of difluoromethyl pyridines from inexpensive materials is reported. The pyridyl subunit is built around the difluoromethyl group rather than a late stage introduction of this moiety. This user-friendly approach allows access to a diverse range of substitution patterns on all positions on the ring system and on the difluoromethyl group.
- Desrosiers, Jean-Nicolas,Kelly, Christopher B.,Fandrick, Daniel R.,Nummy, Larry,Campbell, Scot J.,Wei, Xudong,Sarvestani, Max,Lee, Heewon,Sienkiewicz, Alexander,Sanyal, Sanjit,Zeng, Xingzhong,Grinberg, Nelu,Ma, Shengli,Song, Jinhua J.,Senanayake, Chris H.
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p. 1724 - 1727
(2014/04/17)
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- Synthesis, cytotoxicity, antimicrobial and anti-biofilm activities of novel pyrazolo[3,4-b]pyridine and pyrimidine functionalized 1,2,3-triazole derivatives
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A series of novel pyrazolo[3,4-b]pyridine and pyrimidine functionalized 1,2,3-triazole derivatives 8a-g and 9a-g were prepared starting from 6-trifluoromethylpyridine-2(1H)one 2 via selective O-alkylation, followed by cyclisation using hydrazine hydrate to obtain 6-(trifluoromethyl)-1H-pyrazolo[3, 4-b]pyridin-3-amine 4. Compound 4 was diazotized followed by reaction with sodium azide, resulted in 3-azido-6-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine 5. Compound 5 was further cyclized with N-/O-propargylated pyrimidine derivatives under Sharpless conditions and obtained compounds 6 and 7, respectively. Each set of compounds 6 and 7 were alkylated with different alkyl halides and obtained respective products 8 and 9. All the products were screened for cytotoxicity against four human cancer cell lines such as A549-Lung (CCL-185), MCF7-Breast (HTB-22), DU145-Prostate (HTB-81) and HeLa-Cervical (CCL-2), compounds 9d, 9e and 9f which showed promising activity have been identified. The products were also screened for antimicrobial, anti bio-film and MBC activities. Promising compounds in each case have been identified.
- Nagender,Malla Reddy,Naresh Kumar,Poornachandra,Ganesh Kumar,Narsaiah
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p. 2905 - 2908
(2014/06/10)
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- SUBSTITUTED HETEROCYCLIC AZA DERIVATIVES
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The invention relates to heterocyclic aza derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Page/Page column 89
(2013/03/26)
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- Substituted Heterocyclic Aza Compounds
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Heterocyclic aza compounds as vanilloid receptor ligands, pharmaceutical compositions containing these compounds and also methods of using these compounds for the treatment and/or inhibition of pain and further diseases and/or disorders.
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Paragraph 0631
(2013/03/26)
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- Aryl or N-heteroaryl Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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The invention relates to aryl or N-heteroaryl substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Paragraph 0430; 0431
(2013/04/10)
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- ARYL OR N-HETEROARYL SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to aryl or N-heteroaryl substituted methanesulfonamide derivatives of Formula (I) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Page/Page column 47
(2013/04/13)
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- Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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The invention relates to substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseas
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Paragraph 0265-0266
(2013/04/10)
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- SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted methanesulfonamide derivatives as vanilloid receptor ligands of formula (I), to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and
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Page/Page column 39
(2013/04/13)
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- SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN SO2-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with a S02-containing group as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Page/Page column 67; 68
(2013/05/23)
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- Substituted Heteroaromatic Pyrazole-Containing Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
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Substituted heteroaromatic pyrazole-containing carboxamide and urea compounds as vanilloid receptor ligands, pharmaceutical compositions containing these compounds and also to a method of using these compounds for treating and/or inhibiting pain and further diseases and/or disorders.
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Paragraph 0710
(2013/03/26)
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- Process for the manufacture of halogenated precursors of alkenones and of alkenones
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Process for preparing a halogenated precursor of an alkenone, which comprises reacting a carboxylic acid halide with a vinyl ether in a liquid reaction medium using an equipment having at least one surface in contact with the liquid reaction medium, wherein said surface consists of a material selected from glass, polytetrafluoroethylene and nickel based metal alloy.
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Paragraph 0082
(2013/07/19)
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