- SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF
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The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017
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Paragraph 0032; 0033; 0063; 0067; 0068; 0070; 0072
(2017/09/02)
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- A novel SERS nanoprobe for the ratiometric imaging of hydrogen peroxide in living cells
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In the present study, a novel ratiometric SERS nanosensor via the assembly of 4-mercaptophenylboronic ester on the surface of gold nanorods has been developed and successfully applied in H2O2 imaging in living cells or cancer tissues.
- Peng, Ruiying,Si, Yanmei,Deng, Ting,Zheng, Jing,Li, Jishan,Yang, Ronghua,Tan, Weihong
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p. 8553 - 8556
(2016/07/14)
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- A mild and selective protecting and reversed modification of thiols
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One selective thiol-protecting study has been investigated for a wide range of thiols including general thiols and thiols containing multiple functional groups. The reactions of bromomaleimides and thiols under the mild condition afforded the protected products in excellent yields. The thiols can be recovered very quickly using dithiothreitol (DTT) under the mild condition.
- Li, Xiangmin,Li, Hongxian,Yang, Wei,Zhuang, Jinchen,Li, Hao,Wang, Wei
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supporting information
p. 2660 - 2663
(2016/06/01)
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- Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
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A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.
- Liu, Yajun,Kim, Jihye,Seo, Heesun,Park, Sunghyouk,Chae, Junghyun
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supporting information
p. 2205 - 2212
(2015/07/27)
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- Reductive removal of methoxyacetyl protective group using sodium borohydride
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Herein, we have developed a mild and selective reductive deprotection method for the MAc protected alcohols using sodium borohydride. The new deprotection conditions provide a complete orthogonality between O-MAc and other protecting groups such as tert-butyl ester, N-Boc, Fmoc, Cbz, O-TBDMS, N-benzyl, O-benzyl, O-acetyl, N-acetyl, N-MAc, etc. In addition to O-MAc deprotection, this method is also applicable for S-MAc deprotection.
- Gadekar, Pradip K.,Hoermann, Maryann,Corbo, Faith,Sharma, Rajiv,Sarveswari,Roychowdhury, Abhijit
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p. 503 - 506
(2014/01/06)
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- Thermal reactions of chloroarenes with hydrogen sulfide in the presence of methanol
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Gas-phase reactions of chloroarenes (ClC6H4X, X = H, 4-CH3, 4-OH, 4-Cl, 4-CF3) with hydrogen sulfide or its precursors were investigated in the presence of methanol, which was a stronger H-donor than hydrogen sulfide. Introducing methanol increased the selectivity of arenethiols formation at X = H and 4-CH3 and did not affect the reaction selectivity at acceptor X. The efficiency of methanol influence was considered from the viewpoint of free-radical reaction mechanism and the stability of the arenethiyl radicals. 2005 Pleiades Publishing, Inc.
- Deryagina,Sukhomasova,Levanova,Papernaya,Korchevin
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p. 1624 - 1630
(2007/10/03)
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- Chemoselective protection of thiols versus alcohols and phenols. The Tosvinyl group
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The conjugate addition of aliphatic and aromatic thiols to ethynyl p-tolyl sulphone (tosylacetylene) has been managed to afford Tosvinyl derivatives chemoselectively (in the presence of oxygen nucleophiles) and stereoselectively (isomers Z) in practically quantitative yields. The conditions of choice are: catalytic amounts of Et3N (only 0.5-1.0 mol%), a reaction temperature around 0°C and, for the less acidic thiols, CF3CH2OH or CH3CN/CF3CH2OH as the solvent. Thus, N-Boc-Cys-OMe has been quantitatively protected as its S-Tosvinyl derivative in the presence of N-Boc-Ser-OMe and N-Boc-Tyr-OMe. This novel protecting group is stable to several basic and acidic conditions; its removal is achieved at rt by treatment with an excess of pyrrolidine or at 0°C with alkanethiolate ions.
- Arjona, Odón,Medel, Rocío,Rojas, Jenny,Costa, Anna M.,Vilarrasa, Jaume
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p. 6369 - 6373
(2007/10/03)
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- Substrate mimetics-specific peptide ligases: studies on the synthetic utility of a zymogen and zymogen-like enzymes.
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Although proteases are capable of synthesizing peptide bonds, they are not proficient at peptide fragment ligation. Further manipulations are needed to shift the native enzyme activity from the cleavage to the synthesis of peptides. This account reports on the synthetic potential of nonactivatable trypsinogen and zymogen-like enzymes designed to minimize proteolytic side reactions during peptide synthesis.
- Rall, Kathrin,Bordusa, Frank
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p. 9103 - 9106
(2007/10/03)
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- YELLOW COMPOUND AND WATER-BASED INK-JET RECORDING INK CONTAINING THE COMPOUND
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Aqueous ink for ink-jet recording which contains at least a water-insoluble coloring matter, water and a resin as main components and which takes the form of an emulsion, in which is characterized by containing at least one yellow hue coloring matter selected from the group consisting of a quinophthalone compound represented by the formula (1); and a pyridone azo compound represented by the formula (2); The ink is ink for ink-jet recording having excellent light resistance and storage stability, and enables formation of a high quality image without blotting, and obtained recording image is excellent in water resistance as ink for ink-jet recording.
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- Aqueous ink for ink jet recording
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Aqueous ink for ink jet recording which contains at least a water-insoluble coloring matter, water and a resin as main components and which takes the form of an emulsion, the coloring matter being represented by formula (1) The coloring matter for ink jet recording of the invention is excellent in water resistance in particular and also excellent in light resistance and compatibility with the resin. Thus, it is suited for ink jet recording. Further, the aqueous ink for ink jet recording of the invention which is produced using the coloring matter is excellent in light resistance and storage stability. Especially, when it is used as ink for ink jet recording system, the use of the ink composition can provide excellent aqueous ink that enables formation of a high-quality image without blotting and a recorded image having an excellent water resistance.
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- Process for producing mercaptophenols by the hydrogenolysis of polythiobisphenols
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A novel process for producing mercaptophenols by the hydrogenolysis of polythiobisphenols in the presence of a nickel catalyst is disclosed. Raney nickel catalyst which is in advance poisoned with an organosulfur compound in which the sulfur atom has unshared electron pairs is especially effective as a catalyst. A process for producing polythiobisphenols which comprises: reacting a phenol having the general formula or wherein each R independently represents a hydrogen, a halogen or an alkyl, with sulfur monochloride in a polar organic solvent in the presence of a nitrogen-containing organic compound as a catalyst which is selected from the group consisting of tertiary amines, quaternary ammoniums, alkylated acid amides and heteroaromatic compounds, in amounts of about 1-30 % by weight based on the amount of the phenol used. As a catalyst, bromine or an alkali metal halide is also usable.
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- Cephalosporin compounds and antibacterial agents
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Cephalosporin compounds of the formula (I): STR1 wherein R1 and R2 may be the same or different and are a hydrogen atom or a lower alkyl group of 1-5 carbon atoms and A is a hydrogen atom or a nucleophilic compound residue or pharmacologically acceptable salts thereof have excellent antibacterial activity against Gram positive and Gram negative microorganisms.
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- Process for producing polythiobisphenols and process for producing mercaptophenols by the hydrogenolysis of the same
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A process for producing polythiobisphenols which comprises: reacting a phenol having the general formula STR1 wherein each R independently represents a hydrogen, a halogen or an alkyl, with sulfur monochloride in a polar organic solvent in the presence of a nitrogen-containing organic compound as a catalyst which is selected from the group consisting of tertiary amines, quaternary ammoniums, alkylated acid amides and heteroaromatic compounds, in amounts of about 1-30% by weight based on the amount of the phenol used. As a catalyst, bromine or an alkali metal halide is also usable. A novel process for producing mercaptophenols by the hydrogenolysis of polythiobisphenols in the presence of a nickel catalyst is also disclosed. Raney nickel catalyst which is in advance poisoned with an organosulfur compound in which the sulfur atom has unshared electron pairs is especially effective as a catalyst.
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- HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXVII. REACTIONS OF ALKANETHIONES WITH THE CHLORINE DERIVATIVES OF BENZENE, THIOPHENE, AND NAPHTHALENE
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Alkanethiols react effectively with chlorobenzene, its derivatives, 1-chloronaphthalene, and 2-chlorothiophene at 600-660 deg C with the preferential formation of the corresponding aromatic or heteroatomic thiols.Ethanethiol is most reactive.When it is used instead of hydrogen sulfide in reactions with chlorobenzene or its 4-substituted derivatives, the yield of the aromatic thiols, from which the phenylthiyl radicals are generated with greater difficulty, increases more sharply than the yield of the thiophenols, which generate the more stable 4-XC6H4S radicals.The side products of the reactions are the corresponding diaryl sulfides, thiophene, benzothiophene, and toluene.
- Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.
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p. 755 - 760
(2007/10/02)
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- HIGH TEMPERATURE ORGANIC SYNTHESIS. XIX. MECHANISM OF HIGH-TEMPERATURE REACTION OF AROMATIC CHLORINE DERIVATIVES WITH HYDROGEN SULFIDE
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Quantum-chemical calculations were made in the CNDO/2 approximation for para-substituted chlorobenzene and thiophenol, and the x-ray fluorescence Kα and Kβ spectra of the sulfur in the latter were obtained.The electronic structure parameters of these compounds were compared with their reactivity in high-temperature processess.The reactivity of 4-substituted chlorobenzenes in reaction with hydrogen sulfide in the gas phase correlates with the electron density at the chlorine atom of the chlorine derivative.The direction of this process (the formationof the corresponding thiophenol or diaryl sulfide) is determined by the ability of the thiophenol formed at the first stage to generate sufficiently stable phenylthiyl radicals.The latter are stabilized by a mechanism of ?-conjugation, and the stability increases with increase in the ?-donating character of the para substituent in the aromatic ring. ?-Accepting substituents destabilize the phenylthiyl radicals, increasing the selectivity of the process leading to the production of the respective thiophenol.
- Voronkov, M. G.,Deryagina, E. N.,Dolenko, G. N.,Ivanova, G. M.,Sukhomazova, E. N.,et. al.
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p. 2095 - 2101
(2007/10/02)
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- Rearrangements and decompositions of thiobisphenols
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2,2′-, 2,4′- and 4,4′-Monothiobisphenol separately rearrange in phenol at 180° in the presence of sodium hydroxide to give similar mixtures containing only 2,2′-, 2,4′- and 4,4′-monothiobisphenol in the approximate ratio, 45:45:10. The rearrangements appear to be intermolecular and they are interpreted in terms of polar processes which lead initially to the formation of o- and p-monothiobenzoquinones. 2,2′-Dithiobisphenol, 4,4′-dithiobisphenol and 4,4′-trithiobisphenol under similar conditions are desulphurated with the evolution of hydrogen sulphide also to give mixtures containing only 2,2 - 2,4′- and 4,4′-monothiobisphenol whilst 3,3′-dithiobisphenol is stable in alkaline phenol even after long periods at 180°. Similar initial heterolyses to o- and p-monothiobenzoquinones are suggested as sources of the monothiobisphenols and displacements of sulphide- or hydrosulphide-ions from intermediate benzeneperthiolate ions by carbanions derived from phenol are suggested as sources of the hydrogen sulphide.
- Neale,Bain,Rawlings
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p. 4583 - 4591
(2007/10/05)
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