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1.
In contrast to their carbocyclic aniline analogues, N,N-diarylsubtituted 2-aminothiophenes are not protonated at their N-atoms but at the 5-position or, to a smaller extent, at the 3-position of the thiophene nucleus giving rise to cationic species of the Wheland type. However, 5-formyl and 5-acetyl-substituted 2-(N,N-diarylamino)thiophenes are protonated at the corresponding carbonyl moieties. This finding not only enables insight into the mechanism of electrophilic substitution of N,N-disubstituted 2-aminothiophenes but also allows to prepare deurated 2-aminothiophenes by treatment their non-deuterated parent compounds with CF3COOD. 相似文献
2.
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
3.
M. V. Vovk O. V. Kushnir V. A. Sukach I. F. Tsymbal 《Russian Journal of Organic Chemistry》2010,46(5):709-715
1-Chlorobenzyl isocyanates react with N-arylfumarates with the formation of dialkyl 2-oxo-3,6-diaryl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates that on alkaline hydrolysis are converted into 6-alkoxycarbonyl-1,4-diaryl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acids. The condensation of 1-chloro-1-phenyl-2,2,2-trifluoroethyl isocyanate with N-arylfumarates results in dialkyl 6-oxo-2,3-diaryl-2-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates. 相似文献
4.
Methyl trifluoropyruvate benzene- and methanesulfonylimines react with hex-1-yne and phenylacetylene to give methyl N-sulfonyl-4-oxo-2-trifluoromethyl-4-R-but-2E-enimidates. The reaction mechanism includes the formation of a six-centered bipolar ion followed by its cascade rearrangement. 相似文献
5.
2-Trifluoromethyl-4H-thiochromene-4-thione obtained from 2-trifluoromethyl-4H-thiochromen-4-one and P2S5 reacts with aromatic amines, hydrazine hydrate, phenylhydrazine, and hydroxylamine at the C(4) atom of the chromene ring
to give the corresponding anils, azine, hydrazones, and oxime of thiochromone. 2-Trifluoromethyl-4H-thiochromen-4-one is oxidized by hydrogen peroxide in AcOH into 4-oxo-2-trifluoromethyl-4H-thiochromene 1,1-dioxide and reduced by NaBH4 to 2-trifluoromethyl-4H-thiochromen-4-ol or cis-2-(trifluoromethyl)thiochroman-4-ol. When treated with hydrazine hydrate, thiochromen-4-one gives 3(5)-(2-mercaptophenyl)-5(3)-trifluoromethylpyrazole.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 504–509, March, 2006. 相似文献
6.
V. B. Sokolov A. Yu. Aksinenko T. A. Epishina T. V. Goreva I. V. Martynov 《Russian Chemical Bulletin》2013,62(2):454-455
A cyclocondensation reaction of N-benzoyl- and arenesulfonylimines of methyl trifluoropyruvate with acetylacetone was studied, which led to the formation of 3-substituted 4-acetyl-5-methyl-2-oxo-3-trifluoromethyl-2,3-dihydrofurans. 相似文献
7.
V. B. Sokolov A. Yu. Aksinenko T. A. Epishina T. V. Goreva 《Russian Journal of General Chemistry》2014,84(7):1358-1361
A new method of the synthesis of heterocyclic derivatives of trifluoroalanine based on the cyclocondensation of methyl trifluoropyruvate tert-butoxycarbonylimine with C,N- and N,N-binucleophiles, like Nsubstituted ureas, 1-benzyl-6-aminouracil, benzamidine, and 3-aminocrotononitrile, followed by hydrolysis of the resulting Boc-derivatives to 5-amino-5-trifluoromethylimidazolidine-2,4-diones, 5-amino-5-trifluoromethyl-1-benzyl-5,7-dihydropyrrolo[2,3-d]-pyrimidine-2,4,6-3H-trione, 4-amino-2-methyl-5-oxo-4-(trifluoromethyl)-4,5-dihydro-1H-pyrrole-3-carbonitrile, or 5-amino-5-trifluoromethyl-2-phenyl-3,5-dihydroimidazol-4-one, respectively, was developed. 相似文献
8.
Yoshihisa Kurasawa Ritsuko Katoh Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1992,29(4):1001-1004
The reaction of 6-chloro-2-(1-methylhydrazino)quinoxaline 4-oxide 4a with methyl or phenyl isothiocyanate gave 6-chloro-2-[1-methyl-2-(N-methylthiocarbamoyl)hydrazino]quinoxaline 4-oxide 7a or 6-chloro-2-[1-methyl-2-(N-phenylthiocarbamoyl)hydrazino]quinoxaline 4-oxide 7b , respectively, whose reaction with dimethyl acetylenedicarboxylate afforded 6-chloro-2-[N-methyl-N-(5-methoxycarbonylmethylene-3-methyl-4-oxo-2-thioxoimidazolidin-1-yl)]aminoquinoxaline 4-oxide 8a or 6-chloro-2-[N-methyl-N-(5-methoxycarbonylmethylene-4-oxo-3-phenyl-2-thioxoimidazolidin-1-yl)]aminoquinoxaline 4-oxide 8b , respectively. 相似文献
9.
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
10.
L. M. Potikha A. A. Lysakovskii V. A. Kovtunenko A. V. Turov 《Russian Journal of Organic Chemistry》2009,45(12):1818-1823
5-(4-Chlorophenyl)- and 5-phenylfuran-2(3H)-ones reacted with guanidine carbonate at the methylene group in the unsaturated lactone molecule, leading to the formation
of 4-(2-aryl-5-oxo-2,5-dihydrofuran-2-yl)-5-aryltetrahydrofuran-2-ones, while 5-(4-methylphenyl)furan-2(3H)-one under analogous conditions gave rise to N,N′-bis[4-(4-methylphenyl)-4-oxobutanoyl]guanidine. The reactions of 5-arylfuran-2(3H)- ones with thioacetamide afforded 4-aryl-N-{1-[5-aryl-2-oxo-2,3-dihydrofuran-3-ylidene]ethyl}-4-oxobutanamides. The corresponding N-(4-aryl-4-oxobutanoyl)thioureas were obtained by heating 5-arylfuran-2(3H)-ones with thiourea. 相似文献
11.
Usachev B. I. Usachev S. A. Röschenthaler G.-V. Sosnovskikh V. Ya. 《Russian Chemical Bulletin》2010,59(4):845-847
Treatment of 6-trifluoromethylcomanic acid with sodium hydrosulfide afforded for the first time 4-oxo-6-trifluoromethyl-4H-thiopyran-2-carboxylic acid (6-trifluoromethylthiocomanic acid). When heated or treated with H2SO4, this acid easily underwent decarboxylation leading to 2-trifluoromethyl-4H-thiopyran-4-one. Because of this, both ethyl and methyl 6-tri-fluoromethylthiocomanates were obtained in low yields (15–23%).
Decarboxylation of 6-tri-(di)fluoromethylcomanic acids gave 2-tri(di)fluoromethyl-4H-pyran-4-ones in 77–80% yields. 相似文献
12.
Novel reactions of 7,7-dichloro- and 7,7,8-trichloro-3-oxo-2-oxabicyclo[4.2.0]oct-4-ene-6-carboxylates 5 with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in alcohol gave pyrano[4,3-b]pyran-2,5-diones 8 via (Z)-(2H-pyran-2-on-3-yl)butenoates 7. On the other hand, the same treatment of 7,7,8-trichloro-2-oxo-3-oxabicyclo-[4.2.0]oct-4-ene-5-carboxylate 6b afforded 2-oxo-3-oxabicyclo[4.2.0]oct-4,7-diene-5-carboxylate 14 via cyclobutene formation and SN2′ displacement by attack of the alkoxy anion. 相似文献
13.
4,4-Difluoro-5-trifluoromethyl-2-(2,2,2-trifluoro-1-trifluoromethylethyl)-4H-1,3-dioxine andcis/trans-3-dimethylamino-2-trifluoromethacryloyl fluoride were obtained by reaction ofN-(3,3,3-trifluoro-2-trifluoromethylprop-1-enyl)dimethylamine with MgSO4·7H2O.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1069–1071, May, 1997. 相似文献
14.
Issa Yavari Loghman Moradi Farough Nasiri Hoorieh Djahaniani 《Monatshefte für Chemie / Chemical Monthly》2005,36(9):1757-1761
The regioselective reaction of N1-benzyl-N2-(4-nitrophenyl)ethanediamide with dialkyl acetylenedicarboxylates or alkyl propiolates in the presence of triphenylphosphine
leads to dialkyl 4-benzylamino-1-(4-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylates or alkyl 4-benzylamino-1-(4-nitrophenyl)-2-oxo-5-pyrrolidinecarboxylates in good yields. 相似文献
15.
Ya. V. Zonov V. M. Karpov V. E. Platonov 《Russian Journal of Organic Chemistry》2010,46(10):1517-1526
Perfluorinated 2-methyl- and 2-ethylbenzocyclobutenones on heating in SbF5 underwent isomerization into perfluoroindan-1-one and perfluoro(2-methylindan-1-one), while their reaction with SiO2—SbF5 gave perfluorinated 3-methyl- and 3-ethylphthalides, respectively. Perfluorinated 2-ethyl-2-methyl- and 2,2-diethylbenzocyclobutenones
reacted with SbF5 to produce perfluorinated 2-(but-2-en-2-yl)- and 2-(pent-2-en-3-yl)-benzoic acids, and their transformations in SbF5 over SiO2 afforded 5,6,7,8-tetrafluoro-1-oxo-3-trifluoromethyl-1H-isochromene-4-carboxylic acid and perfluoro(4-ethyl-3-methyl-1H-isochromen-1-one), respectively. 相似文献
16.
Yu. M. Volovenko G. G. Dubnina A. N. Chernega 《Chemistry of Heterocyclic Compounds》2004,40(1):94-100
Reactions of 3,4-dichloro-N-R-maleimides with substituted thiouracils at 40°C gave a 1:1 mixture of isomers of pyrrolothiazolopyrimidinetriones. Under conditions of thermodynamic control (100°C, 5 h) only pyrrolo[3',4':4,5]thiazolo[3,2-a]pyrimidine-4,6,8-triones were formed, hydrolysis of which followed by decarboxylation gave 5-oxo-5H-thiazolo[3,2-a]pyrimidine-2-carboxamide. The structure of N2-phenyl-6-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-2-carboxamide was confirmed by X-ray crystallography. Analogous cyclization of 3,4-dichloro-N-R-maleimides with 2-thioxoquinazol-4-one also gave a mixture of two isomers which were successfully separated by fractional crystallization. 相似文献
17.
Rita Vaickelionienė Vytautas Mickevičius Gema Mikulskienė Maryna Stasevych Olena Komarovska-Porokhnyavets Volodymyr Novikov 《Research on Chemical Intermediates》2011,37(8):1009-1027
N′-(4-Oxo-1,4-dihydronaphthalen-1-ylidene)-1-phenyl-5-oxopyrrolidine-3-carbohydrazides and N′-(3-methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-phenyl-5-oxopyrrolidine-3-carbohydrazides were synthesized by reactions
of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with 1,4-naphthoquinone or 2-methyl-1,4-naphthoquinone. The alkylated analogues
of the above products were obtained using ethyl iodide. The interaction of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with
2,3-dichloro-1,4-naphthoquinone was followed by formation of N′-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1-phenyl-5-oxopyrrolidine-3-carbohydrazides. All these compounds were characterized
using 1H, 13C NMR, IR and mass spectra. Some of the new compounds were tested for the antimicrobial and antifungal activity. 相似文献
18.
The following compounds have been synthesized: 2-Amino-5-trifluoromethyl-1,3,4-thiadiazole; N-(5-trifluoromethyl - 1,3,4-thiadizol-2-yl)benzenesulfonamide; N1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)sulfanilamide, its N4-acetyl, N4-succinyl, and N4-pathalyl derivatives; o - m - and p-trifluoromethylbenzoylthiosemicarbazide, their corresponding 2-amino-1,3,4-thiadiazoles, their corresponding sulfanilamides, their N4-acetyl, N4-succinyl and N4-phthalyl derivatives; 3-o-trifluoromethylphenyl-4H-1,2,4-triazole-5-thiol. Preliminary in-vitro assays show that synthesized sulfanilamide derivatives have antibacterial activity against Staphylococcus aureus. 相似文献
19.
The reactions of 6-nitro-2-trifluoromethylchromone with benzylamine, ethanolamine, and aniline afforded 3-benzyl(2-hydroxyethyl,phenyl)amino-4,4,4-trifluoro-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-ones, respectively, whereas the reactions with ethylenediamine and diethylenetriamine gave rise to 5-(2-hydroxy-5-nitrophenyl)-7-trifluoromethyl-2,3-dihydro-1H-1,4-diazepine and 5-(2-hydroxy-5-nitrophenyl)-7-trifluoromethyl-1,4,8-triazabicyclo[5.3.0]dec-4-ene, respectively. Morpholine added at the double bond of 2-trifluoromethyl- and 6-nitro-2-trifluoromethylchromones to form 2-morpholino-2-trifluoromethylchroman-4-one and its 6-nitro-substituted analog, respectively, whereas piperidine reacted only with 2-trifluoromethylchromone to yield 2-piperidino-2-trifluoromethylchroman-4-one. 相似文献
20.
Synthesis of Novel 2-Aminothiophene-3-carboxylates by Variations of the Gewald Reaction 总被引:1,自引:0,他引:1
Hans-Peter Buchstaller Carsten D. Siebert Ralf H. Lyssy Ina Frank Adil Duran Rudolf Gottschlich Christian R. Noe 《Monatshefte für Chemie / Chemical Monthly》2001,132(2):279-293
Summary. The synthesis of the title compounds through variations of the Gewald reaction is presented. Knoevenagel condensation of methylketone derivatives with methyl cyanoacetate and subsequent treatment of the α,β-unsaturated nitriles
with sulfur and amine resulted in the corresponding 2-aminothiophenes 5 or isomers 9 and 10. Reaction of methylketone derivatives bearing a leaving group at the methyl group under modified Gewald conditions selectively led to the formation of 4-substituted 2-aminothiophenes 9a and 12. The introduction of the sulfur atom occurs through nucleophilic displacement with sodium sulfide.
Received July 5, 2000. Accepted (revised) August 23, 2000 相似文献