- Transition-Metal-Free Aryl-Heteroatom Bond Formation via C-S Bond Cleavage
-
Aryl-heteroatom bonds (C-Het) are almost ubiquitously present in chemical molecules. However, methods for diverse C-Het bond formations from a simple substrate are limited. Herein, we report a convenient and efficient C-S bond transformation of aryl sulfoniums to various C-Het bonds (C-O, C-S, C-Sn, C-Si, C-Se) in the absence of any transition-metal catalyst. These reactions proceeded in mild conditions with a wide substrate scope.
- Zhao, Jian-Nan,Kayumov, Muzaffar,Wang, Dong-Yu,Zhang, Ao
-
p. 7303 - 7306
(2019/10/02)
-
- DYE AND DYEING METHOD
-
A dyeing method is provided, which includes dyeing a dye to a fiber by a supercritical fluid, wherein the dye has a chemical structure of:R 1 is C1-6alkyl group, R 2 is C1-6alkyl group, each of R 3 is independently of H or C1-6alkyl group, and R 4 is a single bond or C1-6alkylene group. When R 4 is single bond, R 5 is. When R 4 is C1-6alkylene group, R 5 is H, Br, Cl, or. Each of R 6 is independently of H, Cl, Br, OCH3, or C1-6alkyl group.
- -
-
Paragraph 0018-0019
(2019/11/16)
-
- Method for preparing p-aminophenyl-beta-hydroxyethyl sulfone sulfate
-
The invention discloses a method for preparing p-aminophenyl-beta-hydroxyethyl sulfone sulfate. The method comprises the following steps: with p-nitrochlorobenzene and mercaptoethanol as basic raw materials, adding into an N,N-dimethylformamide solvent, sufficiently dissolving and uniformly mixing to obtain p-nitrophenyl-beta-hydroxyethyl sulfide, then adding hydrogen peroxide, separating out an oxidization crystallization material, adding solvent water and a palladium-carbon catalyst into the oxidization crystallization material, reacting, filtering to obtain a hydrogenated product and the solvent water, adding the hydrogenated product into an ice-water mixture, diluting, adding pure sulfuric acid, stirring, heating to 150 DEG C, and performing an esterification reaction for 2-3h under avacuum condition to obtain the p-aminophenyl-beta-hydroxyethyl sulfone sulfate after the reaction. The product prepared by the method provided by the invention is high in purity and yield, the raw material consumption is low, the raw material utilization rate is increased, few byproducts are produced and are easy to separate, produced wastewater is easy to treat, and the environmental protection investment is low.
- -
-
Paragraph 0009; 0010; 0011
(2018/04/03)
-
- Preparing methods of p-aminophenyl-beta-hydroxyethylsulfonyl and p-minophenyl-beta-hydroxyethylsulfonyl sulphonate
-
The invention relates to preparing methods of p-aminophenyl-beta-hydroxyethylsulfonyl and p-minophenyl-beta-hydroxyethylsulfonyl sulphonate. The preparing methods both comprise the steps that p-aminophenyl-beta-hydroxyethylsulfonyl and hydrogen are used as raw materials, modified framework nickel is used as a hydrogen-adding catalyst, a catalytic hydrogenation reaction is conducted in a solvent toobtain reduction liquid, and modified framework nickel and the solvent in the reduction liquid are separated and removed to obtain p-minophenyl-beta-hydroxyethylsulfonyl sulphonate; according to modified framework nickel, nickel is used as a framework, and modified framework nickel is prepared from, by mass, 75-95 parts of Ni, 3-15 parts of Al and 2-10 parts of metal adjuvant; the metal adjuvantcomprises the combination of any one or at least two of Mo, Cu and Cr. The yield can reach 94% or above; preparation of p-minophenyl-beta-hydroxyethylsulfonyl sulphonate is a continuous production technology, the technology is simplified, the production efficiency is high, the quality is stable, the production cost is low, and the economic benefit and social benefit are obvious.
- -
-
Paragraph 0099; 0101; 0105; 0107; 0111; 0113; 0117; 0119
(2018/06/21)
-
- Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert -Butyl Nitrite
-
A mild, metal-free synthesis of aryl sulfides has been disclosed. Aryl diazonium ion was generated by the in situ nitrosation of aniline, and it was reduced by ascorbic acid (vitamin C) to form aryl radical, which underwent a thiolation with disulfide to yield aryl sulfide. The reaction proceeded smoothly without heating or irradiation. This strategy was also expanded to the synthesis of aryl selenides.
- Bu, Mei-Jie,Lu, Guo-Ping,Cai, Chun
-
supporting information
p. 1841 - 1846
(2015/08/06)
-
- Synthesis and evaluation of sulfonylethyl-containing phosphotriesters of 3′-azido-3′-deoxythymidine as anticancer prodrugs
-
A series of bis(sulfonylethyl) and mono(sulfonylethyl) phenyl phosphotriesters of zidovudine (3′-azido-3′-deoxythymidine, AZT) were synthesized as potential anticancer prodrugs that liberate AZT monophosphate via nonenzymatic β-elimination mechanism. Stab
- Wang, Jiang,Wang, Yi-Jun,Chen, Zhe-Sheng,Kwon, Chul-Hoon
-
p. 5747 - 5756
(2015/01/09)
-
- Design, Synthesis, and Evaluation of 2-(arylsulfonyl)oxiranes as Cell-permeable Covalent Inhibitors of Protein Tyrosine Phosphatases
-
A structure-based design approach has been applied to develop 2-(arylsulfonyl)oxiranes as potential covalent inhibitors of protein tyrosine phosphatases. A detailed kinetic analysis of inactivation by these covalent inhibitors reveals that this class of compounds inhibits a panel of protein tyrosine phosphatases in a time- and dose-dependent manner, consistent with the covalent modification of the enzyme active site. An inactivation experiment in the presence of sodium arsenate, a known competitive inhibitor of protein tyrosine phosphatase, indicated that these inhibitors were active site bound. This finding is consistent with the mass spectrometric analysis of the covalently modified protein tyrosine phosphatase enzyme. Additional experiments indicated that these compounds remained inert toward other classes of arylphosphate-hydrolyzing enzymes, and alkaline and acid phosphatases. Cell-based experiments with human A549 lung cancer cell lines indicated that 2-(phenylsulfonyl)oxirane (1) caused an increase in intracellular pTyr levels in a dose-dependent manner thereby suggesting its cell-permeable nature. Taken together, the newly identified 2-(arylsulfonyl)oxiranyl moiety could serve as a novel chemotype for the development of activity-based probes and therapeutic agents against protein tyrosine phosphatase superfamily of enzymes.
- Dana, Dibyendu,Das, Tirtha K.,Kumar, Ish,Davalos, Anibal R.,Mark, Kevin J.,Ramai, Daryl,Chang, Emmanuel J.,Talele, Tanaji T.,Kumar, Sanjai
-
p. 489 - 499
(2012/11/06)
-
- Synthesis and second-order nonlinearities of chiral prolinol-substituted chromophores
-
A new series of thiophene- and furan-containing chromophores with a chiral prolinol donor and a sulfone acceptor has been synthesized. The UV-vis absorptions, second-order nonlinear optical properties, and X-ray crystal structures are described.
- Chou, Shang-Shing P.,Yu, Chiung-Yi,Lin, Hong-Cheu,Yang, Pao-Keng
-
p. 487 - 492
(2007/10/03)
-
- BENZAZEPINE DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE
-
The present invention provides a novel benzazepine derivative represented by formula : wherein, R1 is a 5- or 6-membered aromatic ring, R2 is lower alkyl group, etc., Y is an optionally substituted imino group, ring A and ring B are independently an optionally substituted aromatic ring, W is formula -W1-X2-W2- (W1 and W2 are independently S(O)m1 (m1 is 0, 1 or 2), etc., and X2 is an optionally substituted alkylene groupetc. ), a preparation method and use thereof.
- -
-
-
- π-deficient 2-(arylsulfonyl)ethyl esters as protecting groups for carboxylic acids
-
Several π-deficient 2-(arylsulfonyl)ethyl groups have been studied as carboxylic acid protecting groups. The 2-[3,5-bis(trifluoromethyl)phenylsulfonyl]ethyl group is the most easily removed protecting group for acids under mild basic conditions using aqueous NaHCO3.
- Alonso, Diego A.,Nájera, Carmen,Varea, Montserrat
-
p. 277 - 287
(2007/10/03)
-
- Nsc-mediated solid-phase synthesis of polyamides containing pyrrole amino acid
-
The synthesis of the Nsc-protected amino acid, Nsc-Py-OH 1a, and its oligomerization are described.
- Choi, Jin Seok,Lee, Hwa-Sun,Lee, Younjoo,Jeong, Nakcheol,Kim, Hack-Joo,Kim, Young-Deug,Han, Hogyu
-
p. 4295 - 4300
(2007/10/03)
-
- Synthesis and binding properties of oligodeoxynucleotides containing phenylphosphon(othio)ate linkages
-
A method for the synthesis of chimeric oligodeoxynucleotides comprised of phosphodiester and phenylphosphonate [3'O-P(=O)(C6H5)-O-5'] or phenylphosphono-thioate [3'-O-P(=S)(C6H5)-O-5'] linkages has been develope
- Mag, Matthias,Muth, Jochen,Jahn, Kerstin,Peyman, Anusch,Kretzschmar, Gerhard,Engels, Joachim W.,Uhlmann, Eugen
-
p. 2213 - 2220
(2007/10/03)
-
- SYNTHESIS OF C-TERMINAL PEPTIDE FRAGMENTS OF THE HEAVY CHAIN OF HEMAGGLUTININ OF INFLUENZA VIRUS OF SUBTYPES H1 AND H3
-
It is proposed to use the chromogenic 2-ethyl group, which can be eliminated by organic bases in aprotic solvents, for the protection of a C-terminal carboxy group in the synthesis of peptides.The synthesis of a number of 10-1
- Kalashnikov, V. V.,Samukov, V. V.
-
p. 624 - 629
(2007/10/02)
-
- New base-labile amino-protective groups for peptide synthesis
-
Modification of the methyl group in 2-(methylsulphonyl)ethanol gave alcohols which could be used to introduce amino-protective groups of the urethane type, which are labile in alkaline media.The cleavage involves β-elimination.Exchange of the methyl group by a phenyl group bearing a function with a negative inductive effect (NO2 or MeSO2) afforded protecting groups with a higher sensitivity to base.The recommended function is a disulphone: 2-ethanol.The function has a somewhat better stability than the Fmoc group, resists catalytic hydrogenolysis, is highly stable in acidic medium and its elimination product does not polymerize spontaneously.The suggested designation of the new protective group is Mpc.
- Verhart, C. G. J.,Tesser, G. I.
-
p. 621 - 626
(2007/10/02)
-
- Process for producing aminophenyl-β-hydroxyethylsulfone
-
A process for producing aminophenyl-β-hydroxyethylsulfone of the formula (I), STR1 which comprises the following steps: (1) condensing nitrohalobenzene with mercaptoethanol in the presence of an alkali hydroxide and at least one reaction medium selected from N-alkyl-substituted amides and sulfoxides to produce mononitrophenyl-β-hydroxyethylsulfide of the formula (II): STR2 (2) oxidizing the mononitrophenyl-β-hydroxyethylsulfide (II) to produce mononitrophenyl-β-hydroxyethylsulfone of the formula (III): STR3 and (3) reducing the mononitrophenyl-β-hydroxyethylsulfone to produce the aminophenyl-β-hydroxyethylsulfone of the formula (I). This compound is useful as an intermediate for aminophenyl-β-sulfatoethylsulfone represented by the following formula: STR4 which is an important intermediate for vinyl sulfone type reactive dyes largely used for dyeing cellulose fiber materials.
- -
-
-
- ONE-STEP PROTECTION OF THE NUCLEOSIDE BASE IN THYMIDINE AND URIDINE
-
Unprotected thymidine and uridine react with 4-nitrophenylsulfonyl ethene (3) in a base catalyzed Michael type addition to give O4-(4-nitrophenylsulfonylethyl)thymidine (6) and -uridine (7), respectively.The 4-nitrophenylsulfonylethyl group is cleaved within 2.5 hours at 50-55 deg C by concentrated aqueous ammonia, via β-elimination.
- Claesen, C. A. A.,Pistorius, A. M. A.,Tesser, G. I.
-
p. 3859 - 3862
(2007/10/02)
-
- Neighboring-Group Participation by Hydroxyl Oxygen in Nucleophilic Aromatic Substitution. Smiles Rearrangements of (ω-Hydroxyalkyl)methyl(p-nitrophenyl)sulfonium Perchlorates in Aqueous Alkali
-
(2-Hydroxyethyl)- (1), (3-hydroxy-n-propyl)- (2), and (4-hydroxy-n-butyl)methyl(p-nitrophenyl)sulfonium perchlorates (3) were prepared.Products by Smiles rearrangements (intramolecular SNAr reactions) were obtained from 1 as β-(methylthio)ethyl p-nitrophenyl ether (9) in 37-42percent yield and from 2 as γ-(methylthio)propyl p-nitrophenyl ether (8) in quantitative yields, and none were obtained from 3.The rearrangement rates and yields were compared with an intermolecular SN2 reaction of dimethyl(p-nitrophenyl)sulfonium perchlorate (4) (displacement of the sulfonium group by a n-propoxy group) to estimate participation by the ω-hydroxyl oxygen.The rate ratios between the rearrangements (first order) and the SN2 n-propoxy attack (second order), effective molarities, were obtained as 6.02 * 103 M for 1 vs. 4 and 4.64 * 103 M for 2 vs. 4.
- Irie, Tadashi,Tanida, Hiroshi
-
p. 4961 - 4965
(2007/10/02)
-