- Sulfoxide and sulfone compounds, as well as selective synthesis method and application thereof
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The invention discloses a method for selectively synthesizing a sulfoxide compound shown as a formula (II) and a sulfone compound shown as a formula (III). In a reaction solvent, thioether (I) is usedas a reaction raw material and oxygen as an oxidation reagent, under the catalytic action of visible light and a photosensitive reagent; under the assistance of an additive, when a large-polarity proton-containing additive such as an acid and an alcohol or a solvent or an additive with excellent electron donating ability is used, a sulfoxide compound (II) is selectively generated; and when a small-polarity aprotic additive or a solvent is used, a sulfone compound (III) is selectively generated. The synthesis method has the advantages of easily available and cheap raw materials, simple reaction operation, mild reaction conditions, high yield and excellent functional group tolerance. According to the invention, synthesis and modification of some medicines are realized, and an efficient method for selectively constructing sulfoxide and sulfone compounds is provided for medicinal chemistry research.
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Paragraph 0049-0052; 0081-0084
(2019/12/02)
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- Selective Late-Stage Oxygenation of Sulfides with Ground-State Oxygen by Uranyl Photocatalysis
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Oxygenation is a fundamental transformation in synthesis. Herein, we describe the selective late-stage oxygenation of sulfur-containing complex molecules with ground-state oxygen under ambient conditions. The high oxidation potential of the active uranyl cation (UO22+) enabled the efficient synthesis of sulfones. The ligand-to-metal charge transfer process (LMCT) from O 2p to U 5f within the O=U=O group, which generates a UV center and an oxygen radical, is assumed to be affected by the solvent and additives, and can be tuned to promote selective sulfoxidation. This tunable strategy enabled the batch synthesis of 32 pharmaceuticals and analogues by late-stage oxygenation in an atom- and step-efficient manner.
- Li, Yiming,Rizvi, S. Aal-e-Ali,Hu, Deqing,Sun, Danwen,Gao, Anhui,Zhou, Yubo,Li, Jia,Jiang, Xuefeng
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supporting information
p. 13499 - 13506
(2019/08/21)
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- Synthesizing method of 3-sulfonyl alcohol compounds
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The invention discloses a synthesizing method of 3-sulfonyl alcohol compound. The method includes: using substituted sulfohydrazide and propenol compounds as the raw materials to perform reaction in water so as to obtain the 3-sulfonyl alcohol compounds. The method has the advantages that the method uses the substituted sulfohydrazide and the propenol compounds as the raw materials to perform the heating reaction in an aqueous solution without catalysts to directly obtain the 3-sulfonyl alcohol compounds, and the 3-sulfonyl alcohol compounds with the purity being above 80% can be obtained through simple separation after the reaction; the method is few in steps, simple to operate and green, and a new method for synthesizing medical and chemical alcohol compounds is provided for the chemical synthesizing field.
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Paragraph 0014
(2017/04/03)
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- Design of a New Bimetallic Catalyst for Asymmetric Epoxidation and Sulfoxidation
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A new chiral tethered 8-quinolinol-based ligand class is developed. The binuclear titanium complex of the ligand operates through a novel mechanism allowing for the regio- and stereoselective epoxidation of primary and tertiary homoallylic alcohols (up to 98% ee), as well as first examples of 2-allylic phenols (up to 92% ee). The new catalyst system also promotes the asymmetric oxidation of γ-hydroxypropyl sulfides giving an important class of chiral sulfoxides that have been inaccessible to date (up to 95% ee).
- Bhadra, Sukalyan,Akakura, Matsujiro,Yamamoto, Hisashi
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supporting information
p. 15612 - 15615
(2016/01/09)
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- Fluorine-18 Radiolabeling and Radiopharmacological Characterization of a Benzodioxolylpyrimidine-based Radiotracer Targeting the Receptor Tyrosine Kinase EphB4
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Members of the Eph receptor tyrosine kinase family play essential roles in the pathogenesis of cancer and are therefore promising candidates for molecular imaging by positron emission tomography (PET), for example. In this regard, radiochemical access to
- Mamat, Constantin,Mosch, Birgit,Neuber, Christin,K?ckerling, Martin,Bergmann, Ralf,Pietzsch, Jens
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p. 1991 - 2003
(2013/01/15)
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- Catalytic asymmetric hydroboration of heterofunctional allylic substrates: an efficient heterogenized version
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The hydroboration of heterofunctional allylic systems with catecholborane (HBcat) using neutral and cationic rhodium complexes modified with P-P and P-N bidentate chiral ligands has been described in order to produce the secondary heteroorganoboronate ester as a major product with moderate enantioselectivity. The immobilization of cationic chiral rhodium complexes onto clays has beneficial effects on the recyclability and reuse of the catalytic system in particular for the hydroboration of allyl aryl sulfones.
- Lillo, Vanesa,Fernandez, Elena,Segarra, Anna M.
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p. 911 - 914
(2008/02/03)
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- The active role of NHC ligands in platinum-mediated tandem hydroboration-cross coupling reactions
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Stable N-heterocyclic platinum-carbene complexes are the first example of platinum-mediated regioselective H-B addition to vinylarenes and alkynes, allowing consecutive cross coupling reactions with the same catalytic system. The Royal Society of Chemistry.
- Lillo, Vanesa,Mata, Jose A.,Segarra, Anna M.,Peris, Eduardo,Fernandez, Elena
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p. 2184 - 2186
(2008/02/08)
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- Heterofunctional control of regio- and enantioselectivity in rhodium-catalysed hydroboration of allylic systems
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Aryl allylic sulfones were reacted with catecholborane (HBcat) in the presence of neutral and cationic Rh complexes modified with bidentate chiral ligands, to produce the branched heteroorganoboronate ester, as the main isomer with moderate enantioselecti
- Lillo, Vanesa,Fernandez, Elena
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p. 315 - 319
(2007/10/03)
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- Selective oxidation of sulfides to sulfoxides and sulfones at room temperature using H2O2 and a Mo(VI) salt as catalyst
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Selective oxidation of sulfides to sulfoxides and sulfones is achieved by H2O2 using MoO2Cl2 as the catalyst. Various substituted sulfides having functional groups such as methyl, methoxy, bromo, nitro, alkene, alkyne, alcohol, ester, aldehyde and remarkably an oxime are successfully and selectively oxidized without affecting the sensitive functionalities.
- Jeyakumar, Kandasamy,Chand, Dillip Kumar
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p. 4573 - 4576
(2007/10/03)
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- THIOL SULFONE METALLOPROTEASE INHIBITORS
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This invention is directed to proteinase (protease) inhibitors, and more particularly to thiol sulfone inhibitors for matrix metalloproteinase 13(MMP-13), compositions of proteinase inhibitors, intermediates for the syntheses of proteinase inhibitors, processes for the preparation of proteinase inhibitors and processes for treating pathological conditions associated with pathological matrix metalloproteinase activity related to MMP-13.
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- THIOL SULFONE METALLOPROTEASE INHIBITORS
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This invention is directed to proteinase (protease) inhibitors, and more particularly to thiol sulfone inhibitors for matrix metalloproteinase 13(MMP-13), compositions of proteinase inhibitors, intermediates for the syntheses of proteinase inhibitors, processes for the preparation of proteinase inhibitors and processes for treating pathological conditions associated with pathological matrix metalloproteinase activity related to MMP-13.
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- Sulfone Directed Rhodium Catalysed Hydroboration: Regiochemistry in Acyclic System
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Rhodium catalysed hydroboration of allyl sulfones gave rise to Markownikoff product with high regioselectivity.
- Hou, Xue-Long,Hong, Dao-Guang,Rong, Guo-Bin,Guo, Yang-Long,Dai, Li-Xin
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p. 8513 - 8516
(2007/10/02)
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- Generation of hydroxyl radicals from 1-hydroxypyridine-2(1H)-thione and their application to organic synthesis
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Upon irradiation with visible light N-hydroxypyridine-2-thione 1 gives rise to hydroxyl radicals which can be used in radical chain reactions involving selective hydrogen abstraction as the key-step. Key Words: N-hydroxypyridine-2-thione / hydroxyl radicals
- Boivin, J.,Crepon, E.,Zard, S. Z.
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p. 145 - 150
(2007/10/02)
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- N-HYDROXY-2-PYRIDINETHIONE: A MILD AND CONVENIENT SOURCE OF HYDROXYL RADICALS
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N-Hydroxy-2-thiopyridone gives hydroxyl radicals on irradiationm with visible light and these can be incorporated in useful radical chain processes involving hydrogen abstraction.
- Boivin, Jean,Crepon, Elisabeth,Zard, Samir Z.
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p. 6869 - 6872
(2007/10/02)
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- Tetra-n-butylammonium Oxone. Oxidations under Anhydrous Conditions
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Tetra-n-butylammonium Oxone, readily prepared as a white solid from commercially available Oxone, performs oxidations in anhydrous methylene chloride.Under these conditions, sulfides are oxidized to sulfones in the presence of amines, ketones, esters, car
- Trost, Barry M.,Braslau, Rebecca
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p. 532 - 537
(2007/10/02)
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- Synthese de lactones a cycle moyen: Application a la synthese du pentadecanolide-15 et du phoracantholide I
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Medium ring size lactones can be prepared from bifunctional commercial starting compounds in high yields, using a few step sequence.Lactonisation is obtained by cyclization of the free ω-hydroxyacids or by the cyclization of ω-hydroxyacids having the hydroxy and carboxy group protected.
- Cossy, Janine,Pete, Jean-Pierre
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p. 989 - 994
(2007/10/02)
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