- Regioselective C-H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis
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A mild and regioselective method for the preparation of unsymmetrical biaryl sulfides using iron(III) catalysis is described. Activation of N-(arylthio)succinimides using the powerful Lewis acid iron(III) triflimide allowed the efficient thiolation of a range of arenes, including anisoles, phenols, acetanilides, and N-heterocycles. The method was applicable for the late-stage thiolation of tyrosine and tryptophan derivatives and was used as the key step for the synthesis of pharmaceutically relevant biaryl sulfur-containing compounds such as the antibiotic dapsone and the antidepressant vortioxetine. Kinetic studies revealed that while N-(arylthio)succinimides bearing electron-deficient arenes underwent thioarylation catalyzed entirely by iron(III) triflimide, N-(arylthio)succinimides with electron-rich arenes displayed an autocatalytic mechanism promoted by the Lewis basic product.
- Dodds, Amy C.,Sutherland, Andrew
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p. 5922 - 5932
(2021/05/04)
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- Copper complex catalyst and preparation method thereof as well as 4,4 ’ - application of copper complex catalyst in synthesis of diaminodiphenyl sulfone (by machine translation)
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The invention belongs to the technical field of, organic synthesis, and particularly relates to a copper complex catalyst and a preparation method thereof 4,4 ’ - as well as a structural. formula of the copper complex catalyst in catalysis: synthesis of diaminediphenyl sulphone. The preparation method of: the 5 - copper complex catalyst according to the invention has, the advantages that. the copper, complex catalyst, is simple in, synthesis 5 °C step, and 2-4 the, yield of the copper, complex 4,4 ’ - catalyst in the application of the copper complex catalyst in the catalytic synthesis of the diaminodiphenyl sulfone 4,4 ’ - is higher than that of the copper. complex catalyst, 84 - 92%. (by machine translation)
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Paragraph 0019; 0053-0060
(2019/12/31)
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- POLYBENZIMIDAZOLES AND METHODS OF MAKING AND USING THEREOF
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Disclosed are polybenzimidazoles containing sulfonyl groups. The polymers can be synthesized in Eaton's reagent from 3,3′,4,4′-tetraaminodiphenylsulfone, which itself can be synthesized from 4,4′-dichlorodiphenylsulfone. Methods of synthesizing the polymers are disclosed. The disclosed polymers can be used for high temperature H2/CO2 separation membranes and other uses.
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Paragraph 0016; 0127
(2017/04/11)
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- Pentamorphs of acedapsone
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Acedapsone is a long acting prodrug of Dapsone, the diacetyl derivative of diaminophenyl sulfone. It exhibits superior bioavailability compared to the parent drug. Dapsone occupies a preeminent position in the treatment of leprosy since the 1940s. Surprisingly no X-ray crystal structure or polymorphs of acedapsone are reported. Five novel polymorphs of acedapsone are reported (I-V) of which crystal forms I and II are characterized by single X-ray diffraction. These novel polymorphs were crystallized from solution, slow cooling of the melt, and spray-drying of the powder. Solution crystallization afforded Acedapsone Forms I and II. Slow cooling of the melt phase resulted in an amorphous phase, which transformed to a new Form IV slowly at room temperature, and then to Form III. Fast cooling or quick quench of the amorphous solid gave Form I. Spray drying resulted in a new metastable polymorph V, but this polymorph also converted to Form III at room temperature after 6 h. In addition to five crystalline polymorphs of acedapsone, an amorphous phase was also obtained from the melt. XPac analysis of polymorphs I and II (space group P21/n and C2/c) showed 2D isostructurality, and Hirshfeld surface analysis revealed subtle differences in the molecular environment of the two crystal structures. The stability of five polymorphs by DSC, VT-PXRD, and upon heating in a sealed tube suggested that the kinetic stability order is Form I (most stable) > II > III > IV > V > amorphous (least stable), whereas competitive slurry and liquid-assisted grinding experiments gave the thermodynamic stability as Form II (most stable) > I > III > IV > V > amorphous (least stable). Solventless methods such as quench cooling of the melt and holding in a sealed tube at high temperature and pressure yielded the kinetically stable Form I. Spray drying of the powder gave metastable Forms III and V (which transformed over time), and slurry conditions gave the thermodynamic Form II. The pentamorphic system follows Ostwalds law of stages. The role of solvent selection in the direct crystallization of Acedapsone polymorphs after diacetylation of Dapsone is also discussed.
- Bolla, Geetha,Mittapalli, Sudhir,Nangia, Ashwini
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p. 5260 - 5274
(2015/01/09)
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- SOLUBLE PHARMACEUTICAL FORMS OF N,N'-DIAMINODIPHENYL SULPHONE FOR OPTIMUM USE IN THE TREATMENT OF VARIOUS DISEASES
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The present invention aims to demonstrate that a soluble pharmaceutical formulation can be prepared of N,N'-Diaminodiphenyl sulfone which is useful in the development of an ideal drug for use against cerebral infarction, epilepsy, traumatic spinal cord injury, cranio-encephalic trauma, leprosy, Pneumocystis carinii infections and any condition which requires rapid and complete absorption of the compound. A s a representative example of this application, the dissolution of N,N'-Diamino-diphenyl sulfone was evaluated as a neuroprotector in a model of acute cerebral infarction in rats. In this study, N,N'-Diamino-diphenyl sulfone showed significant prevention of brain damage, without presenting adverse effects in animals. It is also shown that the soluble pharmaceutical formulations prepared in this manner produce peak blood levels 30 minutes from oral administration and immediately via the intravenous route.
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- Spinel-type zinc aluminate (ZnAl2O4) nanoparticles prepared by the co-precipitation method: A novel, green and recyclable heterogeneous catalyst for the acetylation of amines, alcohols and phenols under solvent-free conditions
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Zinc aluminate (ZnAl2O4) nanoparticles with an average particle size of about 8 nm were easily prepared by the co-precipitation method using aqueous ammonia solution as the precipitating agent. This nanosized spinel-type oxide was characterized by TGA, XRD, FT-IR, TEM, and surface area measurement and used as the heterogeneous catalyst for the acetylation reaction. Efficient acetylation of various amines, alcohols and phenols was carried out over ZnAl2O4 nanoparticles using acetic anhydride and/or acetyl chloride as the acetylating agents at room temperature without the use of a solvent. The method is highly selective, allowing the alcoholic hydroxyl group to be protected while the phenolic hydroxyl group remains intact, and the amine group can be acetylated in the presence of the hydroxyl group. This method is fast and has a high yield. It is also clean, safe, cost effective, compatible with substrates that have other functional groups and very suitable for practical organic synthesis. In addition, the catalyst can be reused without significant loss of activity. Indeed, the catalytic activity of the ZnAl2O4 nanoparticles is higher than that of bulk ZnAl2O4.
- Farhadi, Saeid,Panahandehjoo, Somayeh
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scheme or table
p. 293 - 302
(2010/09/04)
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- Synthesis and fungicidal activity of bis(2-arylcarbonylamino-1H- benzimidazol-5-yl) sulfones
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A procedure has been developed for the synthesis of bis(2- arylcarbonylamino-1H-benzimidazol-5-yl) sulfones by reaction of the corresponding substituted benzoyl chloride with sodium cyanamide and subsequent treatment of the N-cyanobenzamide thus formed with 3,3′,4,4′- tetraaminodiphenyl sulfone in acid medium. The products were tested for fungicidal activity.
- Pilyugin,Kuznetsova,Sapozhnikov,Chikisheva,Kiseleva,Vorob'eva,Klimakova,Sapozhnikova,Davletov,Galeeva
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p. 446 - 450
(2008/09/19)
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- Synthesis of deuterated 4, 4′-diaminodiphenylsulfone (Dapsone) and related analogs
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A general scheme tor the synthesis ot 4,4′-diaminodiphenylsulfone-d5 (Dapsone) from aniline-d5 is described. The method may have general application and the preparation of the related analogs, 4,4′-dimethylaminodiphenyl sulfone from aniline-d5 and 4,4′-dimethoxydiphenyl sulfone from phenol-d5, is also described. Copyright
- Gannett, Peter M.,Johnson II, Edward M.,Grimes, Michael A.,Myers, Alan L.,Deavers III, Robert E.,Tracy, Timothy S.
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p. 107 - 114
(2007/10/03)
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- Mechanism of oxygenation of aryl methyl and diaryl sulphoxides by peroxomonophosphoric acid
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The kinetics of oxygenation of the title sulphoxides by peroxomonophosphoric acid in aqueous acetic acid follows an overall second-order kinetics, first-order in each reactant. An analysis of the influence of [H+] reveals that H3PO5 is the active species in the oxidation. The structure - reactivity studies with different substituents on the phenyl ring give evidence for the formation of an electron deficient sulphonium ion intermediate as the correlation between log k2 and σ gives a negative ρ value (ρ=-0.47±0.09, r=0.988, s=0.03 at 35°C for aryl methyl sulphoxides and ρ=-0.54±0.11, r=0.983, s=0.07 at 35°C for diaryl sulphoxides). It is proposed that the mechanism involves the nucleophilic attack of the sulphoxide sulphur on the peroxo-oxygen of H3PO5 in the rate-limiting step.
- Suthakaran,Rajagopal,Srinivasan
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p. 1369 - 1374
(2007/10/03)
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- Antiparasitic Agents: Part 5 - Synthesis of 4-(Substituted-aryl)amino-7-chloroquinolines as Potential Antimalarial Agents
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A series of 4-(4- and 3-substituted-aryl)amino-7-chloroquinolines (11-15, 17, 18, 28) and substituted diphenyl sulphones (8-10, 19-27) have been synthesized and tested for their antiparasitic activity against Plasmodium berghei in mice, Litomosoides carinii in cotton rats and Hymenolepis nana in mice.Of the compounds tested, 11 shows 100percent activity against P. berghei at a dose of 10 mg/kg x 5 days in mice while 23 is effective in eliminating 100percent of the H. nana worms from mice at a single oral dose of 250 mg/kg.
- Chauhan, P. M. S.,Sharma, Satyavan,Bhakuni, D. S.
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p. 1142 - 1145
(2007/10/02)
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- Use of Potassium Bromate. Oxidation of Organic Sulphur Compounds
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Oxidation of various organic sulphur compounds by potassium bromate under different experimental conditions was studied.
- Adak, Mohini Mohan,Banerjee, Gopal Chandra,Banerjee, Amalendu
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p. 224 - 228
(2007/10/02)
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