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1.
在Pd(PPh~3)~4/CuI催化下和使用1mol的NEt~3作碱和THF作溶剂,(Z)-3-碘-3-三氟甲基-1-芳基烯丙醇(1)与末端炔烃(3)反应得到正常的偶联产物5。当以NEt~3作碱和溶剂,Pd(PPh~3)~4/CuI催化1与3的交叉偶联反应生成化合物4。4为正常偶联化合物5在NEt~3存在下双键发生重排反应的产物。 相似文献
2.
Secondary esters and those with sterical hindrance at the beta carbon were reacted with base, carbon disulfide, and methyl iodide to produce methyl 2-carboalkoxydithioalkenoate (2). These compounds were reacted with BrF(3), forming the corresponding alpha-trifluoromethyl esters (3) along with 1,1-difluoro-2-trifluoromethyl-2-alkyl ethers (4). The products of type 4 have been transformed to derivatives of type 3, thus raising the overall yields of the target respective alpha-trifluoromethyl esters to 65-80%. The reaction is tolerant to different functional groups such as halogens, protected alcohols, esters, and lactones. 相似文献
3.
D. Shantare M. Yure S. V. Belyakov M. V. Petrova É. Gudrinietse 《Chemistry of Heterocyclic Compounds》1997,33(2):208-215
A convenient method is proposed for the synthesis of new derivatives of the pyridine series, alkyl N-(2-oxo-3-pyridyl)carbamates (IIa-i, IVa-j), in the reaction of 7-trifluoromethyl-5-phenyl-2-oxooxazolo[5,4-b]pyridines (I, IIIa-j) with alcohols.Riga Technical University, Riga LV-1048. Latvian Institute of Organic Synthesis, Riga LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 241–249, February, 1997. 相似文献
4.
E. Suloeva M. Yure E. Gudriniece S. Belyakov M. Petrova I. Kalnite 《Chemistry of Heterocyclic Compounds》2001,37(3):329-337
Syntheses are reported for a series of 2-alkylamino-6-phenyl-4-trifluoromethylpyridines. The reaction of 3-cyano-2-(hydroxyalkylamino)-6-phenyl-4-trifluoromethylpyridines with thionyl chloride gave the corresponding 2-(chloroalkylamino)pyridines, 8-cyano-5-phenyl-7-trifluoromethyl-2,3-dihydro-imidazo[1,2-a]pyridines, and 9-cyano-6-phenyl-8-trifluoromethyl-2,3,4-trihydropyrido[1,2-a]-pyrimidines. X-ray diffraction structural analysis was used to study 8-cyano-5-phenyl-7-trifluoromethyl-2,3-dihydroimidazo[1,2-a]pyridine. 相似文献
5.
Xinjin Li Jingwei Zhao Zhongwei Wang Jianwei Han Jian Zhao Shizheng Zhu 《Tetrahedron》2012,68(38):8011-8017
A Lewis acid promoted nucleophilic substitution reaction between 2-(trifluoromethyl)-2-hydroxy-3-ethoxycarbonyl-2H-chromenes 1 and thiophenols affording thiophenyl substituted products, that is, 4-thiophenyl-2-trifluoromethyl-3-ethoxycarbonyl-4H-chromene and 2-thiophenyl-2-trifluoromethyl-3-ethoxycarbonyl-2H-chromene. 相似文献
6.
Kokotos CG 《The Journal of organic chemistry》2012,77(2):1131-1135
A systematic study to evaluate the ability of various organocatalysts to catalyze the aldol reaction between acetone and 2,2,2-trifluoromethyl-1-phenylethanone was undertaken. Benchmark organocatalysts failed to catalyze this reaction. However, a prolinamide-thiourea consisting of (S)-prolinamide, (1S,2S)-diphenylethylenediamine, and (S)-di-tert butyl aspartate proved to be an efficient catalyst, providing tertiary alcohols as the products of the reaction between ketones and perfluoroalkyl ketones in high to quantitative yields and high enantioselectivities (up 81% ee) at a catalyst loading of 2 mol %. 相似文献
7.
The Lewis acid-promoted reaction of an ethenetricarboxylate derivative (1) with CF3-substituted propargyl alcohols has been examined. Reaction of γ-CF3 propargyl alcohols in the presence of zinc bromide gave five-membered CF3-containing tetrahydrofurans in 66-85% yield. The CF3 group activates alkyne as an electron-withdrawing group. On the other hand, reaction of γ-trifluoromethyl-α-aryl propargyl alcohols 2 with 1 in the presence of 1 equiv of SnCl4 gave cyclobutane derivatives 6 in 29-49% yield. Formation of cyclobutane 6a arises from the [2+2] cycloaddition between ethenetricarboxylate 1 and chloroallene 8, which is produced by the reaction of propargyl alcohol 2a and SnCl4. 相似文献
8.
Resorcinol and 5-methylresorcinol, respectively, react with 3-oxo-2-aryl-4,4,4-trifluorobutyronitrile using zinc chloride as a catalyst in dibutyl ether under the Hoesch reaction conditions to give a low yield of 3-aryl-7-hydoxy-4-trifluoromethyl- or 3-aryl-5-hydroxy-7-methyl-4-trifluoromethyl-2H-l-benzopyran-2-ones. However, the related reaction with m-methoxyphenol was found to produce poor yields of 3-aryl-7-methoxy-4-trifluoromethyl-2H-1-benzopyran-2-one and its 3,4-dihydro-4-hydroxy derivative. 相似文献
9.
Qi Chen 《Tetrahedron》2007,63(48):11965-11972
The asymmetric hydrogenation of a series of 2-(trifluoromethyl)allylic alcohols 1a-g catalyzed by a BINAP-Ru(II) diacetate complex gave the corresponding products 2a-g in high yield (>90% yield) and high diastereoselectivity (>95% de). The asymmetric hydrogenation of 2-(trifluoromethyl)allylic alcohols provided an efficient stereoselective method to construct the 1,1,1-trifluoroisopropyl moiety. Based on the asymmetric hydrogenation of the 2-(trifluoromethyl)allylic alcohol 5a prepared by the reaction of (R)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde with 3,3,3-trifluoroisopropenyllithium, (2R,3S,4R)-4-trifluoromethyl-1-aminopentane-2,3-diol 9 was synthesized in 36% overall yield over five steps. 相似文献
10.
O. G. Kuzueva Ya. V. Burgart V. I. Saloutin O. N. Chupakhin 《Chemistry of Heterocyclic Compounds》2001,37(9):1130-1135
4,5-Bis(hydroxy)-4-trifluoromethyl-6-(fluoroalkyl)hexahydropyrimidin-2-ones (thiones) have been obtained for the first time by the reaction of ureas (thioureas) with di(fluoroalkyl)-substituted 1,3-diketones and tetraols, the dehydration of which gave 2-hydroxy(mercapto)-4-trifluoromethyl-6-(fluoroalkyl)pyrimidines. 相似文献
11.
Treatment of 4-aryl-6-trifluoromethyl-2-pyrones with sodium azide in DMSO afforded the corresponding (Z)-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acids in good yields. Similarly, 4-aryl-3-carbethoxy-6-trifluoromethyl-2-pyrones smoothly reacted with sodium azide in acetonitrile to produce (E)-2-ethoxycarbonyl-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acids in high yields, whereas their reactions in ethanol, accompanied by a configurational change, gave the thermodynamically more stable (Z)-2-ethoxycarbonyl-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acids. 相似文献
12.
L. S. Vasil’ev S. V. Baranin A. V. Ignatenko Yu. V. Nelyubina V. A. Dorokhov 《Russian Chemical Bulletin》2010,59(7):1403-1407
Earlier unknown 4-alkoxy-and 4-hydroxy-5-methyl-4-trifluoromethyl-1,4-dihydropyri-do[4,3-d]pyrimidines were obtained by the reaction of 5-acetyl-4-dimethylaminovinyl-6-(trifluoromethyl)pyrimidine with alcoholic (aqueous)
solutions of NH3. The former eliminate alcohol (water) on sublimation in vacuo to be converted to 5-methyl-4-(trifluoromethyl)-pyrido[4,3-d]pyrimidine. The latter upon the action of alcohols (water) under mild conditions were reverted to the corresponding 4-alkoxy-and
4-hydroxydihydropyrido[4,3-d]pyrimidines. 相似文献
13.
T. V. Frolova D. G. Kim V. V. Sharutin E. N. Shal’kova 《Russian Journal of Organic Chemistry》2016,52(1):96-98
Alkylation of sodium 4(5)-alkyl-6-oxo-1,6-dihydropyrimidine-2-thiolates with 2-bromo-1-(4-bromophenyl)ethan-1-one afforded 2-{[2-(4-bromophenyl)-2-oxoethyl]sulfanyl}pyrimidin-4(3H)-ones. Analogous reaction with sodium 4-trifluoromethyl-6-oxo-1,6-dihydropyrimidine-2-thiolate gave a mixture of 2-{[2-(4-bromophenyl)-2-oxoethyl]sulfanyl}-4-(trifluoromethyl)pyrimidin-4(3H)-one and its intramolecular cyclization product, 3-(4-bromophenyl)-3-hydroxy-7-trifluoromethyl-2,3-dihydro[1,3]thiazolo[3,2-a]-pyrimidin-5-one. 相似文献
14.
A series of aryl 1-(2,6-dimethylphenyl)-2-phenyl-4-trifluoromethyl-5-imidazolyl sulfides was prepared by displacement of fluoride from the 5-position of 1-(2,6-dimethylphenyl)-2-phenyl-4-trifluoromethyl-5-fluoroimidazole by substituted thiophenols and by benzyl mercaptan. This displacement reaction occurs much more slowly than the corresponding previously described reactions of 4-trifluoromethyl-5-fluorothiazoles and -oxazoles. Several solvent-base pairs were examined; the reaction was found to work best when dimethyl sulfoxide was used as the solvent and diazabicycloundecene as the base. The sulfides were oxidized to sulfones by treatment with hydrogen peroxide in acetic acid. 相似文献
15.
Soliman AA 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2007,67(3-4):852-857
Reactions of the cluster compound [Ru(3)(CO)(12)] with 5-trifluoromethyl-2,4-dihydropyrazol-3-one (HL(1)), 4-(2,4-dichlorophenylhydrazono)-5-trifluoromethyl-2,4-dihydropyrazol-3-one (H(2)L(2)), 4-(3-fluorophenylhydrazono)-5-trifluoromethyl-2,4-dihydropyrazol-3-one (H(2)L(3)), 4-(3-trifuoloromethyl-phenylhydrazono)-5-trifluoromethyl-2,4-dihydropyrazol-3-one (H(2)L(4)) and 4-(3-nitrophenylhydrazono)-5-trifluoromethyl-2,4-dihydropyrazol-3-one (H(2)L(5)) have been carried out in benzene and under reduced pressure. The structures of the isolated complexes were elucidated using elemental analyses, IR, UV-vis, mass and NMR spectroscopy. All the complexes are diamagnetic and have trigonal bipyramidal structures with general formulae [Ru(CO)(4)(HL(1))] and [Ru(CO)(3)(H(2)L(2-5))]. The thermal decompositions of the complexes were studied in correlation with the mass spectral fragmentation patterns. 相似文献
16.
V. Yu. Korotaev A. Yu. Barkov M. I. Kodess I. B. Kutyashev P. A. Slepukhin A. Ya. Zapevalov 《Russian Chemical Bulletin》2009,58(9):1886-1898
Reactions of 2-diazo-1,1,1-trifluoro-3-nitropropane or 1-trifluoromethyl-2-nitroethenes with amines and amino alcohols afforded N-mono- and N,N-disubstituted α-trifluoromethyl β-nitro amines, which were used to obtain a number of trifluoromethyl-containing 1,2-diamines, amino alcohols, and β-amino acids. 相似文献
17.
Shu-Su ShenVita Kartika Ying Shan TanRichard D. Webster Koichi Narasaka 《Tetrahedron letters》2012,53(8):986-990
In the presence of copper(I) chloride, tert-butyl 1-hydroxy-2-methyl-6-trifluoromethyl-1H-indole-3-carboxylate acted as a catalyst for the chemoselective aerobic oxidation of allylic and benzylic alcohols. A variety of primary and secondary allylic and benzylic alcohols were oxidized into the corresponding α,β-unsaturated carbonyl compounds in good yields without affecting non-allylic alcohols. 相似文献
18.
3,3-Dialkyl-2,3-dihydro-6-trifluoromethyl-4-pyrones react with hydrazine hydrate to give 2-hydrazino-2-trifluoromethyl-4-tetrahydropyrone hydrazones. When heated, the latter are transformed into 3(5)-(2-hydroxyethyl)-5(3)-trifluoromethylpyrazoles, while their treatment with HCl in ether leads to 3,3-dialkyl-2,3-dihydro-6-trifluoromethyl-4-pyrone azines. 相似文献
19.
The reaction of the 10-I-3 hypervalent iodine electrophilic trifluoromethylation reagent 1-trifluoromethyl-1,2-benziodoxol-3-(1H)-one (2) with 2,4,6-trimethylphenol, after deprotonation with NaH and in the presence of 18-crown-6 in a polar, nonprotic solvent, affords 1,3,5-trimethyl-2-(trifluoromethoxy)benzene (4) only as a byproduct. Trifluoromethylation occurs preferentially at the ortho- and para-positions of the aromatic core, giving the corresponding trifluoromethylcyclohexadienones 5 and 6. In case the ortho- and/or para-positions are not substituted, the corresponding products of an aromatic, electrophilic substitution are obtained in moderate yield, for example, 2-trifluoromethyl-4-tert-butylphenol (10a) from 4-tert-butylphenol (10). 相似文献
20.
E. P. Doronina L. M. Pevzner V. A. Polukeev M. L. Petrov 《Russian Journal of General Chemistry》2017,87(3):447-455
By adding diethyl hydrogen phosphite to 5-trifluoromethyl-2-furaldehyde (5-trifluoromethylfur-2-yl)(diethoxyphosphoryl)methanol was synthesized. It was oxidized with DMSO-acetic anhydride mixture to diethyl 5-trifluoromethyl-2-furoyl phosphonate. The reaction of the latter with ethoxymethylenetriphenylphosphorane gives ethyl (2E)-3-(diethoxyphosphoryl)-3-(5-trifluoromethylfur-2-yl)propenoate. Analogous reaction of (diethoxyphosphoryl)(5-trifluoromethylfur-2-yl)acetic aldehyde yields ethyl (4E)-4-(diethoxyphosphoryl)-4-(5-trifluoromethylfur-2-yl)-but-3-enoate. The addition of nitromethane to these esters of unsaturated acids in the presence of potassium fluoride gives a mixture of diastereomers of phosphorylated esters of 2-nitromethyl-3-(5-trifluoromethylfur-2-yl)propanoic and 3-nitromethyl-4-(5-trifluoromethylfur-2-yl)butanoic acids respectively. By the reduction of ethyl nitropropanoate with zinc and formic acid in dioxane ethyl 2-aminomethyl-3-(diethoxyphosphoryl)-3-(5-trifluoromethylfur-2-yl)propanoate was prepared in a low yield. It may be considered as the derivative of β-alanine containing additional pharmacophore fragments. 相似文献