- Behavior of Trifluoroacetohydrazonoyl Bromide in Basic Media
-
The bromide 1 was treated with sodium methoxide or phenoxide to give exclusively the corresponding substituted product.The predominant formation of the substituted products was also recognized with regard to various amines.However, the reaction with triet
- Tanaka, Kiyoshi,Maeno, Seiji,Mitsuhashi, Keiryo
-
-
Read Online
- 2-(Halogenated Phenyl) acetamides and propanamides as potent TRPV1 antagonists
-
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
-
-
- Novel trifluoromethylated spiro-1,3,4-thiadiazoles via [3+2]-cycloadditions of 2,3-diphenylcyclopropenethione with selected in situ-generated nitrile imines derived from trifluoroacetonitrile
-
The in situ-generated N-aryl nitrile imines derived from trifluoroacetonitrile react efficiently with 2,3-diphenylcyclopropenethione to give spirocyclic 1,3,4-thiadiazole derivatives as products of a regio- and chemoselective [3+2]-cycloaddition in good t
- Utecht-Jarzyńska, Greta,Jasiński, Marcin,?wia?tek, Kamil,Mlostoń, Grzegorz,Heimgartner, Heinz
-
p. 251 - 262
(2020/02/03)
-
- Trapping of trifluoroacetonitrile imines with mercaptoacetaldehyde and mercaptocarboxylic acids: An access to fluorinated 1,3,4-thiadiazine derivatives via (3+3)-annulation
-
The in situ generated highly electrophilic nitrile imines derived from trifluoroacetonitrile are efficiently trapped by monomeric mercaptoacetaldehyde at room temperature in THF solution. The initially formed 1:1 adducts undergo spontaneous cyclization le
- Utecht-Jarzyńska, Greta,Michalak, Aleksandra,Bana?, Justyna,Mlostoń, Grzegorz,Jasiński, Marcin
-
-
- Mannich reaction of trifluoroacetaldehyde hydrazones: A useful entry to trifluoromethyl substituted heterocycles
-
NH-aryl hydrazones derived from trifluoroacetaldehyde hemiacetal may be involved in efficient Mannich type reactions with formaldehydes and aromatic aldehydes. The resulting hydrazones are useful building blocks for the preparation of trifluoromethyl substituted heterocycles as shown by a straightforward preparation of 1,2-diazine derivatives under heating with β-ketoesters.
- Jia, Shuanglong,El Kaim, Laurent
-
supporting information
p. 1457 - 1460
(2018/03/08)
-
- Polysubstituted 3-trifluoromethylpyrazoles: Regioselective (3 + 2)-cycloaddition of trifluoroacetonitrile imines with enol ethers and functional group transformations
-
Non-catalysed addition of trifluoroacetonitrile imines to enol ethers provided fully regioselectively (3 + 2)-cycloadducts, which either spontaneously or via Br?nsted acid-induced elimination of ROH molecules led to the formation of 3-trifluoromethylated
- Utecht, Greta,Fruziński, Andrzej,Jasiński, Marcin
-
supporting information
p. 1252 - 1257
(2018/03/06)
-
- Expected and unexpected results in reactions of fluorinated nitrile imines with (cyclo)aliphatic thioketones
-
A series of (cyclo)aliphatic thioketones have been tested towards trifluoroacetonitrile imines, generated in situ via base-induced dehydrohalogenation of the respective hydrazonoyl bromides. Typically, non-enolisable thioketones yielded exclusively 3-trif
- Utecht, Greta,Sioma, Justyna,Jasiński, Marcin,Mlostoń, Grzegorz
-
-
- Trifluoromethylated 2,3-dihydro-1,3,4-thiadiazoles via the regioselective [3+2]-cycloadditions of fluorinated nitrile imines with aryl, hetaryl, and ferrocenyl thioketones
-
A series of hydrazonoyl bromides prepared from readily available N-arylhydrazones of fluoral was used for the in situ generation of fluorinated nitrile imines. These 1,3-dipoles were efficiently trapped with aryl and hetaryl thioketones yielding fluoromet
- Mlostoń, Grzegorz,Urbaniak, Katarzyna,Utecht, Greta,Lentz, Dieter,Jasiński, Marcin
-
p. 147 - 154
(2016/11/25)
-
- Tautomeric equilibrium in trifluoroacetaldehyde arylhydrazones
-
Abstract A series of p-substituted phenylhydrazones of trifluoroacetaldehyde (1) was synthesized and the azo-hydrazo (1-2) tautomeric equilibrium was investigated experimentally using correlation analysis and computationally with DFT methods. Investigation revealed strong impact of the substituent and solvent polarity on the tautomeric ratio (1/2). Calculations also revealed that acidity of the azo tautomers is similar to that of malonate esters.
- Wojciechowska, Agata,Jasiński, Marcin,Kaszyński, Piotr
-
p. 2349 - 2356
(2015/03/30)
-
- Synthesis of polysubstituted pyrazoles by a platinum-catalyzed sigmatropic rearrangement/cyclization cascade
-
A highly efficient Pt-catalyzed [3,3] sigmatropic rearrangement/cyclization cascade of N-propargylhydrazones is reported. The process provides expedient access to a variety of highly functionalized pyrazoles. The substrate has good substituted group compa
- Wen, Jia-Jie,Tang, Hai-Tao,Xiong, Kai,Ding, Zong-Cang,Zhan, Zhuang-Ping
-
supporting information
p. 5940 - 5943
(2015/01/08)
-
- Solvent-free stereoselective synthesis of (E)-trifluoromethyl imines and hydrazones
-
A new, green and efficient strategy for the synthesis of trifluoromethyl ketimines, aldimines, and hydrazones starting from the corresponding trifluoromethyl carbonyl compounds or their hemiacetals is reported. The condensation reactions were performed under solvent-free conditions with a range of amines or hydrazines and proceeded with high stereoselectivity, always giving only the E-isomer in very good yields. Georg Thieme Verlag Stuttgart - New York.
- Carroccia, Laura,Fioravanti, Stefania,Pellacani, Lucio,Tardella, Paolo A.
-
experimental part
p. 4096 - 4100
(2011/02/21)
-
- VIRAL POLYMERASE INHIBITORS
-
Compound of Formula I: wherein, R2, R5 and R6 are defined herein, are useful as inhibitors of the hepatitis C virus NS5B polymerase
- -
-
Page/Page column 98
(2009/04/25)
-
- Viral Polymerase Inhibitors
-
Compounds of formula I: wherein X, R2, R3, R5 and R6 are defined herein, are useful as inhibitors of the hepatitis C virus NS5B polymerase.
- -
-
Page/Page column 49
(2008/06/13)
-
- Electrolytic Reactions of Fluoro Organic Compounds. 7. Anodic Methoxylation and Acetoxylation of 2,2,2-Trifluoroethyl Sulfides. Preparation of Highly Useful Trifluoromethylated Building Blocks
-
Anodic methoxylation and acetoxylation of 2,2,2-trifluoroethyl sulfides and the corresponding nonfluorinated sulfides were comparatively studied.It was found that a trifluoromethyl group remarkably promoted anodic substitution and methoxy and acetoxy groups were introduced adjacent to the trifluoromethyl group of the sulfides.Longer perfluoroalkyl groups also promoted these anodic substitutions.These products were shown to be highly useful building blocks fro the synthesis of fluoro organic compounds.
- Fuchigami, Toshio,Yamamoto, Kayoko,Nakagawa, Yuki
-
p. 137 - 142
(2007/10/02)
-
- Synthesis and Reaction of 5-Amino-3-trifluoromethylisoxazole and -pyrazole-4-carboxylic Acids
-
5-Amino-3-trifluoromethylisoxazole- and -pyrazole-4-carboxylic acids were prepared by the reactions of trifluoroacetonitrile oxide or -imines with cyanoacetic acid derivatives, respectively.The behavior of thus obtained aminoazole-4-carboxylic acids towar
- Tanaka, Kiyoshi,Suzuki, Takashi,Maeno, Seiji,Mitsuhashi, Keiryo
-
p. 1535 - 1538
(2007/10/02)
-
- ELECTROLYTIC TRANSFORMATION OF FUNCTIONAL GROUPS OF FLUOROORGANIC COMPOUNDS. I. ANODIC METHOXYLATION AND ACETOXYLATION OF TRIFLUOROETHYL SULFIDE
-
Anodic methoxylation and acetoxylation of phenyl trifluoroethyl sulfide were successfully performed to give the corresponding α-methoxy and α-acetoxy sulfides in good to excellent yields, respectively.These products were found to be useful building blocks
- Fuchigami, Toshio,Nakagawa, Yuuki,Nonaka Tsutomu
-
p. 3869 - 3872
(2007/10/02)
-
- Cycloadditions of N-Aryl-C-(Trifluoromethyl)nitrilimines with Dimethyl Fumarate and Maleate
-
The cycloadditions of N-aryl-C-(trifluoromethyl)nitrilimines 1, generated in situ from various precursors, with dimethyl fumarate and maleate are described.N-Aryltrifluoroacetohydrazonoyl bromides 2 reacted with fumarate in the presence of triethylamine to give the trans-4,5-dimethoxycarbonylpyrazolines 4 whereas the reactions with maleate afforded the 4,5-dimethoxycarbonylpyrazoles 5 as well as 4.In the reactions with the chloride 6 under the more drastic conditions, both fumarate and maleate gave the pyrazole 5a.From thermolysis of the oxadiazaphosphole 8, thetrans-pyrazoline 4a was formed in both cases of fumarate and maleate.The preparation of the cis-pyrazoline 9 was attempted from 8 and maleic anhydride but 9 was found to be so unstable as to be epimerized under the mild conditions.
- Tanaka, Kiyoshi,Maeno, Seiji,Mitsuhashi, Keiryo
-
p. 565 - 568
(2007/10/02)
-
- Arylazo(R)methaniminoxyls, an Example of a "NO 3-Electron ? Bond"?
-
According to the IR and NMR results, a series of partly labelled arylazoaldehyde oximes (5a - 25a) are either only (primary compound 5a, aliphatic aldehyde oxime derivatives 7a - 13a) or predominantly (14a - 25a) E,E compounds (26a).Their dehydrogenation
- Neugebauer, Franz Alfred,Umminger, Irmgard
-
p. 3706 - 3718
(2007/10/02)
-
- PREPARATION OF TRIFLUOROACETONITRILE PHENYLAMINE AND ITS REACTIONS WITH SOME DIPOLAROPHILES
-
Trifluoroaceto-N-phenylhydrazonoyl halides, the precursors of trifluoroacetonitrile phenylamine, prepared by halogenation of trifluoroacetaldehyde phenylhydrazon, react with various olefins and acetylenes in the presence of triethylamine to give 3-trifluo
- Tanaka, Kiyoshi,Maeno, Seiji,Mitsuhashi, Keiryo
-
p. 543 - 546
(2007/10/02)
-