13616-82-5Relevant articles and documents
Synthesis method of substituted thiophenol (by machine translation)
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, (2020/06/09)
The invention provides a method for synthesizing substituted thiophenol, which comprises the following steps of preparing compound V compound and NaHSO3 Or KHHSO3 Reaction synthesis IV compound, compound of formula IV and SO2 Reaction-synthesis III compounds of formula III are passed NaBH in NaOH solution. 4 Of formula II is reduced and the compound of formula II is acidified to give a compound of formula I. The method for synthesizing the substituted thiophenol has the advantages of greenness, high efficiency, easiness in industrial application and the like. (by machine translation)
Synthesis and biological evaluation of some bicyclic [2-(2,4-dimethylphenylthio)phenyl] aniline and its amide derivatives as potential antitubercular agents
Patil, Yogesh,Shingare, Ramesh,Chakraborty, Shakti,Borkute, Rachana,Sarkar, Dhiman,Madje, Balaji
, (2018/02/27)
Abstract: In the present investigation, a series of bicyclic [2-(2,4-dimethylphenylthio)phenyl] aniline analogues were synthesized and characterized by IR, NMR (1H and 13C) and mass spectra. All newly synthesized 15 compounds were inspected for their in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H 37Ra in both active and dormant state using an established XTT Reduction Menadione assay (XRMA). The titled compounds exhibited minimum inhibitory concentration (MIC90) ranging from 0.05 to?>30 (μ g/mL). The potent four compounds were further evaluated in THP-1 infection model where they demonstrated significant antitubercular activity. All the ex vivo active were further evaluated for cytotoxic activity against THP-1, MCK-7 and HeLa cell lines in order to check selectivity index. All compounds were further screened against four different bacteria to assess their selectivity towards MTB. These derivatives could be considered as a precursor structure for further design of antituberculosis agent. Graphical Abstract: SYNOPSIS A series of bicyclic [2-(2,4-dimethylphenylthio)phenyl] aniline analogues were synthesized. All newly synthesized 15 compounds were inspected for their in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H 37Ra in both active and dormant state using an established XTT Reduction Menadione assay (XRMA).[Figure not available: see fulltext.].
Copper versus thioether-centered oxidation: Mechanistic insights into the non-innocent redox behavior of tripodal benzimidazolylaminothioether ligands
Martínez-Alanis, Paulina R.,Sánchez Eguía, Brenda N.,Ugalde-Saldívar, Víctor M.,Regla, Ignacio,Demare, Patricia,Aullón, Gabriel,Castillo, Ivan
supporting information, p. 6067 - 6079 (2013/07/05)
A series of Cu+ complexes with ligands that feature varying numbers of benzimidazole/thioether donors and methylene or ethylene linkers between the central nitrogen atom and the thioether sulfur atoms have been spectroscopically and electrochemically characterized. Cyclic voltammetry measurements indicated that the highest Cu2+/Cu+ redox potentials correspond to sulfur-rich coordination environments, with values decreasing as the thioether donors are replaced by nitrogen-donating benzimidazoles. Both Cu2+ and Cu+ complexes were studied by DFT. Their electronic properties were determined by analyzing their frontier orbitals, relative energies, and the contributions to the orbitals involved in redox processes, which revealed that the HOMOs of the more sulfur-rich copper complexes, particularly those with methylene linkers (-N-CH2-S-), show significant aromatic thioether character. Thus, the theoretically predicted initial oxidation at the sulfur atom of the methylene-bridged ligands agrees with the experimentally determined oxidation waves in the voltammograms of the NS3- and N2S2-type ligands as being ligand-based, as opposed to the copper-based processes of the ethylene-bridged Cu+ complexes. The electrochemical and theoretical results are consistent with our previously reported mechanistic proposal for Cu 2+-promoted oxidative C-S bond cleavage, which in this work resulted in the isolation and complete characterization (including by X-ray crystallography) of the decomposition products of two ligands employed, further supporting the novel reactivity pathway invoked. The combined results raise the possibility that the reactions of copper-thioether complexes in chemical and biochemical systems occur with redox participation of the sulfur atom. Copyright
Non-aqueous reduction of aromatic sulfonyl chlorides to thiols using a dichlorodimethylsilane-zinc-dimethylacetamide system
Uchiro, Hiromi,Kobayashi, Susumu
, p. 3179 - 3182 (2007/10/03)
A new and efficient method for the non-aqueous reduction of sulfonyl chlorides to affored the corresponding thiols by use of a dichlorodimethylsilane-zinc-dimethylacetamide system was successfully developed. Various aromatic thiols were prepared in high yield by easy operation. Continuous reactions with the above reduction using the prepared thiol were also demonstrated.
Catalytic kinetic resolution of 5-alkoxy-2(5H)-furanones
Faber, Wijnand S.,Kok, Johan,De Lange, Ben,Feringa, Ben L.
, p. 4775 - 4794 (2007/10/02)
The kinetic resolution of racemic 5-alkoxy-2(5H)-furanones, using a chiral aminoalcohol catalyzed 1,4-addition of arylthiols, was examined. Using various butenolides it was shown that a γ-alkoxy substituent appears to be essential to reach high enantioselectivities whereas electron-donating substituents in the arylthiols also increase the selectivity. Cinchona alkaloids are the preferred catalysts for the kinetic resolution, with quinine and quinidine leading to the most efficient and selective thiol additions. A remarkable dilution effect and a strong dependency on the mode of addition of reactants were observed. Optimization studies are presented of the kinetic resolution of 5-methoxy-2(5H)-furanone 2 resulting in (R)-2 or (S)-2 with enantiomeric excesses exceeding 90%. A mechanism for the quinine (quinidine) catalyzed kinetic resolution is given.
REDUCTION OF SULFONIC ACIDS WITH TRIPHENYLPHOSPHINE-DIARYL DISULFIDE SYSTEM.
Oae,Togo
, p. 232 - 236 (2007/10/02)
Diaryl disulfides are effective catalysts to reduce arenesulfonic acids with triphenylphosphine to the corresponding arenethiols in good yields, while alkanesulfonic acids are transferred into the corresponding alkyl aryl sulfides. Arenesulfonic acids bearing electron-donating substituents can be reduced more readily than those having electron-withdrawing substituents, while diaryl disulfides bearing electron-withdrawing substituents are more effective catalysts than diaryl disulfides with electron-donating ring substituents.
The Synthesis of All of the Dimethyldibenzothiophenes and Monoethyldibenzothiophenes
Tedjamulia, Marvin L.,Tominaga, Yoshinori,Castle, Raymond N.
, p. 1485 - 1495 (2007/10/02)
The synthesis of all four isomers of the monoethyldibenzothiophenes and all of the sixteen isomers of the dimethyldibenzothiophenes has been accomplished.
Reduction of Sulfonic Acids and Related Organosulfur Compounds with Triphenylphosphine-Iodine System
Oae, Shigeru,Togo, Hideo
, p. 3802 - 3812 (2007/10/02)
Arenesulfonic acids, their sodium salts, and alkyl arenesulfonates can be reduced readily to the corresponding arenethiols quantitatively by treatment with a mixture of triphenylphosphine and a catalytic amount of iodine, while alkanesulfonic acids, sulfinic acids, disulfides, thiosulfonic S-esters, and sulfonates are also readily reduced to the corresponding thiols similarly.Upon treatment with a mixture of triphenylphosphine and excess iodine, however, these aliphatic sulfur compounds are converted eventually to the corresponding alkyl iodides.The relative reactivities of these sulfonyl derivatives in the reaction with the triphenylphosphine-iodine system are the following.Aromatic series: ArSO2Cl, ArSO2SAr' > ArSO2H > ArSO3R > ArSO3-HNBu3+ (or PyH+) > ArSO3H > ArSO2SO2Ar >> ArSO2CH2C(CH3)3, ArSO3Ar'.Aliphatic series: RSO2Cl, RSO2SR', RSO2-HNBu3+ > RSO3-HNBu3+ > RSSR, RSO2H > RSO3H > RSH > RSO3R'.In these reactions, the arenesulfonic acids bearing electron-donating substituents can be reduced more readily than those having electron-withdrawing substituents.
REDUCTION OF SULFONIC ACIDS WITH PHOSPHORUS PENTASULFIDE
Oae, Shigeru,Togo, Hideo
, p. 4701 - 4704 (2007/10/02)
Arene, and alkanesulfonic acids are easily reduced to the corresponding polysulfides R-(S)n-R (n= 2.9 3.3) by treatment with phosphorus pentasulfide.In this reaction, the formation of both P-O-S and P-S-H linkages is considered to be involved in the key step of the reduction.
IODINE CATALYZED REDUCTION OF ARENESULFONIC ACID TO THE ARENETHIOL WITH TRIPHENYLPHOSPHINE
Fujimori, Ken,Togo, Hideo,Oae, Shigeru
, p. 4921 - 4924 (2007/10/02)
Arenesulfonic acids, its sodium salts, and alkyl arenesulfonates were reduced readily to the corresponding arenethiols quantitatively with triphenylphosphine in the presence of iodine.
