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1.
N-(2,2,2-Trichloroethylidene)- and N-(2,2,2-trichloroethyl)arenesulfonamides react with phenol, 2-chlorophenol, and 2-methylphenol in the presence of oleum or sulfuric acid to give the corresponding 4-(2,2,2-trichloro-1-arylsulfonylaminoethyl)phenols in good yields.  相似文献   

2.
The interaction of N-(1-aryl-2,2,2-trichloroethyl)amides of arenesulfonic acids with secondary amines or their salts in the presence of inorganic bases involves the formation of chloroaziridine intermediates. Depending upon the solvent and reagent ratio, the reaction results in N-[1-dialkylamino-2-chloro-2-arylethylidene]-, N-[2-dialkylamino-1-chloro-2-arylethylidene]-, N-[1,2-bis(dialkylamino)-2-arylethylidene]-, and N-(1,2-dioxo-2-arylethene)amides of arenesulfonic acids.  相似文献   

3.
Chlorination of 2-thiophenesulfonamide gave unstable N,N-dichloro-2-thiophenesulfonamide which was brought into reactions with 1,2-polyhaloethenes. The condensation of 2-thiophenesulfonamide with trichloroacetaldehyde afforded N-(2,2,2-trichloro-1-hydroxyethyl)-2-thiophenesulfonamide which reacted with benzene, toluene, 2-chlorothiophene, and phenol to form the corresponding N-(1-aryl-2,2,2-trichloroethyl)-2-thiophenesulfonamides. Under more severe conditions, the latter were converted into 1,1-diaryl-2,2,2-trichloroethanes. The reaction of N-(2,2,2-trichloro-1-hydroxyethyl)-2-thiophenesulfonamide with substituted arenes, including phenol, was regioselective: only the corresponding para-substituted products were obtained. Hydrolysis of N-[2,2,2-trichloro-1-(4-tolyl)ethyl]-2-thiophenesulfonamide yielded N-(2-thienylsulfonyl)-2-(4-tolyl)glycine.  相似文献   

4.
A new method for the synthesis of N-substituted 2-(4-oxo-4,5,6,7-tetrahydroindol-3-yl)acetic acids was developed. Alkylation of cyclic 1,3-diketones with 3,5,5,5-tetrachloropentan-2-one affords 1,4-diketones, which undergo cyclization with different primary amines into N-substituted 3-(2,2,2-trichloroethyl)-4,5,6,7-tetrahydroindol-4-ones. Acid hydrolysis of the latter gives the corresponding indol-3-ylacetic acids. The structures of the compounds obtained were confirmed by 1H and 13C NMR data.  相似文献   

5.
Highly reactive N-(2,2,2-trichloroethylidene)nitrobenzenesulfonamides were synthesized by reaction of N,N-dichloronitrobenzenesulfonamides with trichloroethylene. Reactions of N-(2,2,2-trichloroethylidene)nitrobenzenesulfonamides with oxygen and nitrogen nucleophiles gave products of addition at the double CÍN bond; with arenes and haloarenes, the corresponding C-amidoalkylation products were obtained.  相似文献   

6.
Reactions of N-(2,2,2-trichloroethyl)arenesulfonamides with primary alkyl bromides and iodides, allyl bromide, chloroacetonitrile, and benzyl chloride in acetonitrile on heating in the presence of potassium carbonate gave the corresponding N-alkyl-N-(2,2,2-trichloroethyl)arenesulfonamides.  相似文献   

7.
An IR study of thiocarboxylic acid N-(1-arenesulfonamido-2-phenyl-2,2-dichloroethyl- and -2,2,2-trichloroethyl)amides revealed intramolecular hydrogen bonds whose formation is accompanied by electron density delocalization and stabilization of conformations with quasiaromatic rings. Formation of chelate species was confirmed by AM1 calculations.  相似文献   

8.
N-(2,2,2-Trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides react with an equimolar amount of biuret to give 1-(1-arylsulfonylamino-2,2,2-trichloroethyl)- or 1-(1-arylsulfonylamino-2,2-dichloro-2-phenylethyl)biurets. The reactions with 2 equiv of N-(polychloroethylidene)arenesulfonamides involve both amino groups in the biuret molecule, yielding the corresponding 1,5-bis(1-arylsulfonylamino-2,2,2-trichloroethyl)- and 1,5-bis(1-arylsulfonylamino-2,2-dichloro-2-phenylethyl)biurets.  相似文献   

9.
C-Amidoalkylation of aroxy- and arylsulfanylacetic acids and their methyl esters was effected by reaction with N-(2,2,2-trichloro-1-hydroxyethyl)sulfonamides and -carboxamides in the presence of methane- or trifluoromethanesulfonic acids as catalyst and solvent. The process is regioselective, and the substitution occurs at the para-position with respect to the heteroelement-containing group.  相似文献   

10.
Xiao-Shu He  Arnold Brossi 《合成通讯》2013,43(14):2177-2179
2,2,2-Trichloroethyl chloroformate (1) in higher boiling solvents, particularly in the presence of potassium carbonate and potassium bicarbonate, affords undesired di-(2,2,2-trichloroethyl)-carbonate (2) as a byproduct. When chemically pure chloroformate was used, addition of carbonates was found to be unnecessary in N-demethylation reactions.  相似文献   

11.
Quantum-chemical calculations (B3LYP/6-311G**) of N-(1-trifluoromethylsulfonylamino-2,2,2-trichloroethyl)acrylamide CF3SO2NHCH(CCl3)NHC(O)CH=CH2 (I) in the isolated state revealed four local minima corresponding to the conformers with the syn- and antiperiplanar orientation of the C=O and N-H bonds in the amide fragment, two of which containing the intramolecular C(O)NH…O=S or SO2NH…O=C hydrogen bonds. Judged from the data of IR spectroscopy and dielectrometry, compound I in inert media exists predominantly in the form of conformer with antiperiplanar amide fragment and free NH group. Its self-associates in molecular crystals and solutions are formed by hydrogen bonds SO2NH…O=C. Spectroscopic acidity of compound I determined as the value of Δν(NH) upon interactions with DMF in CCl4 is higher than that of N-methyltrifluoromethanesulfonamide.  相似文献   

12.
Hydrolytic transformations of 4-[2,2,2-trichloro-1-(arylsulfonylamino)-and-(ethoxycarbonylamino)ethyl]phenyloxy(or sulfanyl)acetic acids under microwave irradiation in alkaline medium involve both trichloromethyl group and ester fragment to give N-arylsulfonyl-2-[4-carboxymethyloxy(or sulfanyl)phenyl]-2-aminoacetic acids in good yields. Hydrolysis of methyl 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl)acetates without microwave activation occurs only at the ester group with quantitative formation of 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl) acetic acids. N-[2,2,2-Trichloro-1-(1-naphthyl, 2-furyl, and 1-methylindol-3-yl)ethyl]-4-chlorobenzenesulfonamides in alkaline medium under microwave irradiation were converted in 10–15 min into the corresponding N-(4-chlorophenylsulfonyl)-2-aryl-2-aminoacetic acids in preparative yields.  相似文献   

13.
N-(2,2,2-Trichloroethylidene)- and N-(2-phenyl-2,2-dichloroethylidene)amides of aromatic sulfonic acids react with thioacetamide, thiourea, and N-acetylthiourea at equimolar reagents ratio to furnish N-(1-arenesulfonamido-2,2,2-trichloroethyl)- and N-(1-arenesulfonamido-2-phenyl-2,2-dichloroethyl)thioamides. The reaction with deficient amount of thiourea results in N,N'-bis(1-arenesulfonamido-2-polychloroethyl)-thiocarbamides.  相似文献   

14.
N-(2,2,2-Trichloroethylidene)-, N-(2,2-dichloro-2-phenylethylidene)-, and N-(1-hydroxy-2-polychloroethyl) arenesulfonamides reacted with adamantane in carbon tetrachloride in the presence of oleum or concd. H2SO4-P4O10 mixture to give the corresponding N-(2-polychloroethyl)arenesulfonamides as a result of reduc-tion of the azomethine and OH group, respectively.  相似文献   

15.
The reaction of N,N-dichloromethanesulfonamide with trichloroethylene gave N-(2,2,2-trichloro- ethylidene)trifluoromethanesulfonamide which showed high reactivity toward oxygen- and nitrogen-centered nucleophiles, as well as in C-alkylation of aromatic compounds.  相似文献   

16.
The first method for the synthesis of the title compounds has been established. Quantitative reactions of benzamides with chloral hydrate provided chloralbenzamides which were efficiently converted to N-(1,2,2,2-tetrachloroethyl)amides by treatment with phosphorus pentachloride. These compounds reacted selectively with alcohols under mild conditions to give N-(1-alkoxy-2,2,2-trichloroethyl)benzamides in high yields which were stereoselectively transformed to (E)-4-alkoxy-2-aryl-5-chloro-2-oxazolines in fair to good yields by electrochemical reduction under constant cathodic potential in an aprotic medium.  相似文献   

17.
N-(2,2,2-Trichloro-1-hydroxyethyl)- and N-(2,2-dichloro-1-hydroxy-2-phenylethyl)arenesulfonamides are oxidized with chromium(VI) oxide to give, respectively, N-(arylsulfonyl)trichloroacetamides and N-(arylsulfonyl)dichloro(phenyl)acetamides. Under analogous conditions N-(2,2,2-trichloro-1-hydroxyethyl)trifluoromethanesulfonamide is converted into 1,1,1-trichloro-2,2-bis(trifluoromethylsulfonylamino)ethane.  相似文献   

18.
5-Amino-1-aryl-4-methylpyrazoles readily add to methyl 1-aryl-2,2,2-trifluoroethylidenecarbamates to give the corresponding methyl 1-aryl-2,2,2-trifluoro-1-(5-pyrazolylamino)ethylcarbamates which undergo fragmentation at elevated temperature in the presence of an organic base to afford N-(5-pyrazolyl)-1-aryl-2,2,2-trifluoroethanimines.  相似文献   

19.
1-Aryl-1-chloro-2,2,2-trifluoroethyl)-N'-(p-tolyl)carbodiimides treated with triethylamine undergo intramolecular cyclization into 4-aryl-6-methyl-2-triethylammonio-4-trifluoromethyl-4-dihydroquinazolidines.  相似文献   

20.
Conclusions The esterification of amido- and ester-amidophosphites with 1-(2-thienyl)-2,2,2-trichloroethanol gave the l-(2-thienyl)-2,2,2-trichloroethyl dialkyl- and 1-(2-thienyl)-2,2,2-trichloroethyl alkylamidophosphites, which easily add sulfur or are oxidized to the corresponding thiophosphates and phosphates.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 182–187, January, 1981.  相似文献   

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