- 2-benzylthio-aniline croconic acid cyanine chemical sensor capable of identifying Hg and preparation method of chemical sensor
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The invention relates to a 2-benzylthio-aniline croconic acid cyanine chemical sensor capable of identifying Hg and a preparation method of the chemical sensor. The preparation method comprises steps as follows: 2-benzylthio-aniline is synthesized from 2-aminothiophenol and benzyl chloride, and a 2-benzylthio-aniline croconic acid cyanine dye compound is synthesized from 2-benzylthio-aniline and croconic acid. The chemical sensor and the preparation method have beneficial effects as follows: the synthetic process is relatively simple, reaction conditions are easy to control, and the prepared 2-benzylthio-aniline croconic acid cyanine dye has excellent optical performance and optical stability. When the 2-benzylthio-aniline croconic acid cyanine dye is used for identifying Hg, colorof a solution also changes besides change of an absorption spectrum, so that the 2-benzylthio-aniline croconic acid cyanine dye has a colorimetric identification function and facilitates detection for Hg. Besides, the 2-benzylthio-aniline croconic acid cyanine dye has good selectivity and anti-interference performance for identification of Hg.
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Paragraph 0022-0023; 0025-0026
(2019/04/30)
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- Iron(ii)-catalyzed sulfur directed C(sp3)-H bond amination/C-S cross coupling reaction
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An efficient iron(ii)-catalyzed sulfur directed C(sp3)-H bond amination/C-S cross coupling reaction has been developed. The reaction had high tolerance of functional groups under moderate conditions. The results of a deuterium labeling study and in situ ESI-MS experiments indicated that the reaction mechanism probably corresponds to a Fe(ii)/Fe(iii) catalytic cycle.
- Duan, Fang-Fang,Song, Shi-Qian,Xu, Run-Sheng
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p. 2737 - 2739
(2017/03/10)
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- Eco-compatible three component strategies for C-S bond formation in thioether and S-aryl-carbamodithioate compounds catalyzed by copper(II) nanoparticles supported on modified AlPO4
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One-pot and three components C-S bond formation reactions in thioethers and S-aryl-carbamodithioates have been catalyzed by a copper heterogeneous nano-catalyst supported on modified AlPO4 under different reaction conditions. The above-mentioned nano-catalyst has been characterized by various techniques such as SEM, TEM, AFM, XRD, FT-IR, UV–Vis, CV, BET, TGA, ICP and XPS spectrometry and its particle size was estimated to be between 60–110?nm. Finally, the reusability of the catalyst up to ten cycles without any significant leaching is one of the outstanding properties of the catalyst.
- Sharghi, Hashem,Ghaderi, Iman,Doroodmand, Mohammad Mahdi
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- Palladium nanoparticles stabilized by aqueous vesicles self-assembled from a PEGylated surfactant ionic liquid for the chemoselective reduction of nitroarenes
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Vesicles self-assembled from an aqueous PEGylated surfactant ionic liquid solution can be applied for stabilizing palladium nanoparticles, which prove to be an efficient catalytic system for chemoselective hydrogen transfer of nitroarenes using hydrazine hydrate as a hydrogen source. The particle sizes of vesicles are decreased with the increase of ionic liquid's concentrations and relatively small particle sizes are beneficial to the reduction. Moreover, the aqueous catalytic system still stays in reactor by simple extraction, and is reused without further treatment.
- Xu, Zhu-bing,Lu, Guo-ping,Cai, Chun
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- The invention relates to a thiourea as the sulfur source synthesis of substituted 2 - aryl benzo thiazole
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The invention discloses a method for synthesizing poly-substituted 2-aryl benzothiazoles by utilizing thiourea as a sulphur source. According to the method, thiourea reacts with benzyl chloride to generate an S-benzylisothiourea salt in situ. After that, through the aromatic nucleophilic substitution reaction of the obtained S-benzylisothiourea salt with 2-fluoronitrobenzene and then the one-step reduction (one-pot reaction) process, o-amino phenyl benzyl thioether as an intermediate product can be obtained. Finally, through the iron-catalyzed cross-dehydrogenative-coupling reaction of the o-amino phenyl benzyl thioether, a target product can be obtained. Compared with the traditional synthetic method, the method has the significant advantages of (1) short reaction step, wherein the target product can be synthesized through only three steps of simple reactions by utilizing simple chemical raw materials; (2) mild reaction condition, high atom economy, and relatively safe and cheap reaction reagents; (3) high reaction yield, good substrate tolerance and free of any dangerous or high-toxicity reagent. Therefore, the method might be applied to the large-scale production.
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Paragraph 0019; 0020
(2017/08/25)
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- Radical Route to 1,4-Benzothiazine Derivatives from 2-Aminobenzenethiols and Ketones under Transition-Metal-Free Conditions
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Transition-metal-free radical access to 1,4-benzothiazine derivatives from o-aminobenzenethiols is disclosed. This procedure is available for various ketones including α,β-unsaturated, cyclic, linear, and fluoroalkyl ketones to generate a number of 1,4-benzothiazines, which exist in numerous bioactive and natural molecules, rendering this protocol attractive to both synthetic and medicinal chemistry.
- Lin, Ya-mei,Lu, Guo-ping,Wang, Rong-kang,Yi, Wen-bin
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supporting information
p. 6424 - 6427
(2016/12/23)
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- Ortho-Aminothiophenol Compounds and Uses Thereof
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A method for treating or preventing a microbial infection in a subject in need thereof, the method comprising administering to the subject, a therapeutically effective amount of a compound of Formula Ia, a compound of Formula IIa, one or more compounds of Formula Ia or Formula IIa complexed with a metal core, or a pharmaceutically acceptable salt, prodrug or hydrate thereof.
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Paragraph 0279-0281
(2014/12/09)
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- An odorless, one-pot synthesis of nitroaryl thioethers via SNAr reactions through the in situ generation of S-alkylisothiouronium salts
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A newly developed C-S bond formation nucleophilic aromatic substitution (SNAr) reaction in aqueous Triton X-100 (TX100) micelles has been disclosed. This chemistry, in which odorless, cheap and stable thiourea in place of thiols is used as the sulfur reagent, provides an efficient approach for the generation of nitroaryl thioethers, which are useful structural units of many bioactive molecules, rendering this methodology attractive to both synthetic and medicinal chemistry.
- Lu, Guo-Ping,Cai, Chun
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p. 59990 - 59996
(2015/02/19)
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- DFT and experimental study of the structure and vibrational spectra of 2-(benzylthio)-N-{pyridinylmethylidene}anilines
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2-(Benzylthio)-N {pyridine-4-ylmethylidene}aniline was prepared by reaction of S-benzyl ortho-aminothiophenol with 4-pyridine carboxaldehyde and characterized by NMR, IR and Raman spectroscopy and mass spectrometry. The structure and the vibrational analysis of the series of 2-, 3-, and 4-pyridine derivatives was performed based on a comparative computational methodology study with the density functionals B3LYP and B3PW91 and the basis sets LanZ2DZ and 6-31++G(d,p). Comparison of computational results with single crystal X-ray diffraction results of 2-(benzylthio)-N {pyridine-3-ylmethylidene}aniline allowed the evaluation of structure predictions and confirmed B3PW91/6-31++G(d,p) as most accurate for structure determination of the four investigated levels of theories. B3LYP and B3PW91 with the LanL2DZ basis set consistently outperformed calculations for IR and Raman vibrational estimations when compared to level of theories using the 6-31++G(d,p) basis set. Application of scaling factors for IR and Raman frequency predictions showed excellent agreement with experimental values and supported the assignment of the major contributors of the vibration modes of the three pyridine pendant compounds. Overall, B3PW91/LanL2DZ level of theory showed best performance in accuracy and low computational cost for structural and vibrational analysis for the series of 2-(benzylthio)-N-{pyridinylmethylidene}anilines.
- Alberto Acosta-Ramirez,Larade, Mathew C.,Lloy, Samantha M.,Cross, Edward D.,McLellan, Beth M.,Martell, Jaime M.,McDonald, Robert,Bierenstiel, Matthias
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- Bidentate coordination behaviour of a potentially tridentate ligand. A mononuclear four-coordinate Ni(II) complex supported by two o- iminobenzosemiquinonato units
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Using a new N,O,S-potentially tridentate ligand (H2L), a mononuclear NiII complex of composition II [Ni (L-? )2 ], (1) has been synthesized. The structure of the complex has been elucidated in the solution state using 1H NMR spectroscopy and in the solid state by X-ray crystallography. X-ray studies reveal that the NiII is surrounded by two o-iminobenzosemiquinonate(1-) p-radical ligands, providing a NiIIN2O2 square planar coordination environment. Notably, the thioether unit in each ligand remains non-coordinated. Cyclic voltammetric measurements of (1) show two one-electron reductive and two one-electron oxidative redox responses, which are ligand-centred in origin. Characterization of electrochemically-generated reduced and oxidized species has also been accomplished.
- Mukherjee, Atasi,Mukherjee, Rabindranath
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experimental part
p. 484 - 490
(2011/06/20)
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- Synthesis and characterization of donor-functionalized N,S-compounds containing the ortho -aminothiophenol motif
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A series of twenty S-benzyl ortho-aminothiophenol and S,S-xylylene-bridged bis(ortho-aminothiophenol) compounds and their imine derivatives have been synthesized in moderate to excellent yields and characterized. The syntheses were optimized, including large-scale syntheses, and an improved purification method involving the HCl salt was developed. This paper also serves as a comprehensive review of xylylene-bridged bis(ortho-aminothiophenol) compounds. Georg Thieme Verlag Stuttgart New York.
- Cross, Edward D.,Shehzad, Usman A.,Lloy, Samantha M.,Brown, Adam R. C.,Mercer, Todd D.,Foster, Daniel R.,McLellan, Beth L.,Murray, Alexander R.,English, Margaret A.,Bierenstiel, Matthias
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experimental part
p. 303 - 315
(2011/03/18)
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- Privileged structures: Synthesis and structural investigations on tricyclic sulfonamides
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Customized synthetic procedures for the obtainment of highly functionalizable free sulfonamide tricyclic structures having NH, O, S and SO2 (Z group) in the central seven-membered ring are presented. Due to the role that tricycles and the sulfonamide group play in medicinal chemistry, attention have been also paid to the 3D arrangement of these molecules. Their molecular structures and conformational properties have been studied by single-crystal X-ray diffraction and quantum chemical methods (HF-SCF/6-311+G(d,p). The minimum energy geometries in the solid state (I, Z = O; II, Z = NH and III, Z = S, SO2) have been compared with the minimum-energy geometries in the gas phase (invariably the type III geometry) and discussed with respect to the literature reference values. An effort was made to correlate the conformational differences observed in the solid-state and gas-phase with the nature of the Z grouping.
- Altamura, Maria,Fedi, Valentina,Giannotti, Danilo,Paoli, Paola,Rossi, Patrizia
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scheme or table
p. 2219 - 2231
(2011/04/23)
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- Design and synthesis of cinanserin analogs as severe acute respiratory syndrome coronavirus 3CL protease inhibitors
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The severe acute respiratory syndrome (SARS) coronavirus 3CL protease is an attractive target for the development of anti-SARS drugs. In this paper, cinanserin (1) analogs were synthesized and tested for the inhibitory activities against SARS-coronavirus (CoV) 3CL protease by fluorescence resonance energy transfer (FRET) assay. Four analogs show significant activities, especially compound 26 with an IC50 of 1.06 μM.
- Yang, Qingang,Chen, Lili,He, Xuchang,Gao, Zhenting,Shen, Xu,Bai, Donglu
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scheme or table
p. 1400 - 1405
(2009/09/29)
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- A facile one-pot preparation of alkyl aminoaryl sulfides for the synthesis of GW7647 as an agonist of peroxisome proliferator-activated receptor α
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We have developed two simple and high yielding one-pot syntheses of alkyl aminoaryl sulfides containing a series of four-steps: in situ protection of the free amine by reaction with a Grignard reagent, halogen-lithium exchange, sulfur insertion, and a substitution reaction with various electrophiles. Through this protocol, we have successfully synthesized tert-butyl-2-[4-(2-aminoethyl) phenylsulfanyl]-2-methylpropanoate, a key intermediate for the synthesis of GW7647 and GW9578 (ureido-TiBAs), in 92% yield. Furthermore, we were able to improve the overall yield of, GW7647 to 66%, 3 times the yield previously reported.
- Ham, Jungyeob,Cho, Sung Jin,Ko, Jaeyoung,Chin, Jungwook,Kang, Heonjoong
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p. 5781 - 5784
(2007/10/03)
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- π-aromatic and sulfur nucleophilic partners in cationic π-cyclizations: Intramolecular amidoalkylation and thioamidoalkylation cyclization via ω-carbinol lactams
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NaBH4 reduction of imides 1 and 6a,b,c followed by a π-cyclization of the resultant N-acyliminium ions, generated in trifluoroacetic acid conditions, afforded two positional isomers, isoindolobenzothiazolinones 4 and 8, respectively. These ring closures proceeded via an intramolecular α-amidoalkylation with the classical α-aromatic or the atypical sulfur atom as an internal nucleophile. A ready access to the related six-membered N,S-heterocyclic compounds such as isoindolobenzothiazinones 20a and 21a is also described. During this reaction, we have shown that ω-carbinol lactam precursor 14a led to endocyclic and exocyclic N-acyliminium ions 18a and 19a in equilibrium via the cyclic aza-sulfonium ion A. The latter furnished the expected products 20a and 21a in good yields. Similarly, different ω-carbinol lactams 14b-e substituted at C-angular position afforded the corresponding isoindolobenzothiazinones 20b-e and 21b-e bearing an angular alkyl, aralkyl, or aryl group. In the case of methyl 14b and benzyl 14e groups, an additional amount of the dehydration products 16b and 31 was isolated. These results indicate that the isomerization-π-cyclization takes place via the cleavage of the thioether linkage in acidic medium.
- Hucher,Decroix,Daich
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p. 4695 - 4703
(2007/10/03)
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- A new approach to reductive deprotection of thioethers with a low-valent titanium reagent
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Low-valent titanium mediated cleavage of carbon-sulphur bond is reported. This has resulted in an efficient and mild protocol for the deprotection of allyl/benzyl thioethers under reductive condition and with good yields. Deprotection can be performed regio- and chemo-selectively in the presence of acid, ester and N-benzyl/allyl functionalities and is general for aliphatic and aromatic precursors.
- Shadakshari,Talukdar,Chattopadhyay
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p. 1007 - 1010
(2007/10/03)
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- An interrupted Pummerer reaction induced by hypervalent iodine(III) reagent: A new synthesis of pyrrolo[2,1-b]benzothiazole
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Treatment of 1-(2-alkylthiophenyl)pyrroles with phenyliodine(III) bis(trifluoroacetate) containing trifluoroacetic acid resulted in an interrupted Pummerer reaction to give pyrrolo[2,1-b]benzothiazole rather than the normal Pummerer-type products.
- Chen, Ling-Ching,Wang, Huey-Min,Kang, Iou-Jiun
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p. 1437 - 1441
(2007/10/03)
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- SYNTHESIS OF 2-SUBSTITUTED 2,3-DIHYDRO-1,4-BENZOTHIAZINE-3-THIONES VIA IMINOPHOSPHORANES
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2-(Substituted methylsulfanyl)anilines (5) were treated with triphenylphosphine dibromide to yield iminophosphoranes (6), whose aza-Wittig reaction with carbon disulfide gave 2-(substituted methylsulfanyl)phenyl isothiocyanates (8).Cyclization of 8 by strong bases afforded 2-substituted 2,3-dihydro-1,4-benzothiazine-3-thiones (10).
- Takahashi, Masahiko,Ohba, Masaru
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p. 2263 - 2270
(2007/10/03)
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- Synthesis and Biological Activity of 4-(Diphenylmethyl)-α--1-piperazineethanol and Related Compounds
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A series of 4-(diphenylmethyl)-α--1-piperazineethanol and closely related compounds was synthesised and evaluated for cardiac and vascular activity in isolated perfused rat and guinea pig hearts.Compound 1 produced greater inotropic effects in rat hearts than in guinea pig hearts, a phenomenon which was also observed with the prototype agent DPI 201-106.Compound 15 produced an inotropic effect with one-tenth the potency of compound 1.Both compounds 1 and 15 demonstrated direct inotropic and vasodilatory effects when administered iv in anesthetized dogs, although the vasodilatory activity was more pronounced with compound 15 than 1 and DPI compound.Compound 1 lacks the CN moiety which is a key structural requirement in DPI for positive inotropic activity.The synthesis, in vitro, and in vivo evaluations of these agents, and comparative data with DPI-201-106 (compound 17) are reported.
- Sircar, Ila,Haleen, Steve J.,Burke, Sandra E.,Barth, Hubert
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p. 4442 - 4449
(2007/10/02)
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- SYNTHESIS OF 6H-DIBENZOTHIOPYRAN-6-OL via PSCHORR REACTION AND ITS CONVERSION TO THE CORRESPONDING 6-CARBOXY AND 6-(1-PIPERAZINYL) DERIVATIVES
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6H-Dibenzopyran-6-carboxylic acid described in a preceding communication was an intermediate to compounds provided of immunomodulating and hypolipidemic activity.The synthesis of the thio analogue 8 is now reported.The key intermediate, 6H-dibenzothiopyran-6-ol, 6, was obtained via Pschorr cyclization and Pummerer rearrangement.In comparison with the corresponding 6H-dibenzopyran-6-ol, compound 6 was less reactive toward some nucleophiles.
- Banzatti, Carlo,Melloni, Piero,Salvadori, Paolo
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p. 259 - 262
(2007/10/02)
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