cas 873-55-2, Sodium benzenesulfinate | Articles data

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Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.
Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
p. 8338 - 8342
(2021/10/25)

2-AMINO-N-(AMINO-OXO-ARYL-LAMBDA6-SULFANYLIDENE)ACETAMIDE COMPOUNDS AND THEIR THERAPEUTIC USE
The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain 2-amino-N-(amino-oxo-aryl-λ6- sulfanylidene)acetamide compounds (referred to herein as ANASIA compounds) that, inter alia, inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase (aaRS) (e.g., bacterial leucyl-tRNA synthetase, LeuRS). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase; to treat disorders that are ameliorated by the inhibition (e.g., selective inhibition) of bacterial aminoacyl-tRNA synthetase; to treat bacterial infections; etc.
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Page/Page column 107

(2021/06/26)

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis
An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.
Cui, Wenwen,Jiang, Min,Lv, Jian,Song, Xiuyan,Sun, Kai,Xu, Guiyun,Yan, Qiuli,Yang, Daoshan
supporting information
p. 3663 - 3668
(2021/05/31)

Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process
Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.
Li, Yuxiu,Li, Xiangqian,Li, Xiaowei,Shi, Dayong
supporting information
p. 2152 - 2155
(2021/03/06)

Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis
N-Heterocyclic carbene (NHC) catalysis has emerged as a versatile tool in modern synthetic chemistry. Further increasing the complexity, several processes have been introduced that proceed via dual catalysis, where the NHC organocatalyst operates in concert with a second catalytic moiety, significantly enlarging the reaction scope. In biological transformations, multiple catalysis is generally used to access complex natural products. Guided by that strategy, triple catalysis has been studied recently, where three different catalytic modes are merged in a single process. In this Communication, direct α-C-H acylation of various alkenes with aroyl fluorides using NHC, sulfinate, and photoredox cooperative triple catalysis is reported. The method allows the preparation of α-substituted vinyl ketones in moderate to high yields with excellent functional group tolerance. Mechanistic studies reveal that these cascades proceed through a sequential radical addition/coupling/elimination process. In contrast to known triple catalysis processes that operate via two sets of interwoven catalysis cycles, in the introduced process, all three cycles are interwoven.
Liu, Kun,Studer, Armido
supporting information
p. 4903 - 4909
(2021/05/04)

Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol
Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.
Chen, Yi-Xuan,Wang, Zhu-Jun,Xiao, Jun-An,Chen, Kai,Xiang, Hao-Yue,Yang, Hua
supporting information
p. 6558 - 6562
(2021/08/23)

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron
The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.
Qiu, Di,Li, Songyi,Yue, Guanglu,Mao, Jinshan,Xu, Bei,Yuan, Xinyu,Ye, Fei
supporting information

(2021/11/04)

Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates
This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.
Cheng, Lan,Guo, Jianbo,Li, Yufei,Liang, Xin,Wang, Qingmin,Xia, Qing,Zhang, Pei,Zhang, Weihua
supporting information
p. 8865 - 8870
(2021/11/30)

Styrene sulfone NLRP3 inflammasome inhibitor, preparation method and application thereof
The invention relates to the field of styrene sulfone compounds and NLRP3 inhibitors, and particularly provides a styrene sulfone NLRP3 inflammasome inhibitor, a preparation method and application thereof, wherein the inhibitor is represented by a formula (1), n is selected from 0 and 1, X is selected from N and O, R1 is selected from different electron withdrawing or electron donating substituents, and R2 is selected from different fat or aromatic substituents. According to the invention, it is verified that the compounds represented by the general formula have NLRP3 inhibitory activity.
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Paragraph 0053; 0068-0071; 0076-0077

(2020/10/30)

Preparation method of substituted sulfinate
The invention discloses a preparation method of substituted sulfinate, which comprises the following steps: by using substituted sulfonyl chloride as a raw material, carrying out hydrolysis reductionreaction on the substituted sulfonyl chloride in water in the presence of a reducing agent and an acid-binding agent to generate the corresponding substituted sulfinate. The method is a novel method which is easy to implement and suitable for industrial scale production and is used for preparing sulfinate and derivatives thereof. The method is simple in technological process, high in product purity and safe and environment-friendly, wherein the waste gas, solid and liquid are easy to treat.
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Paragraph 0023-0025; 0029-0031

(2020/12/30)

Synthetic method of zinc benzenesulfinate
The invention discloses a synthetic method of zinc benzenesulfinate. The method comprises the following steps: S1, reducing benzenesulfonyl chloride into benzenesulfinate in the presence of an inorganic base by using the benzenesulfonyl chloride as a starting raw material, sodium sulfite as a reducing agent and water as a solvent to obtain a benzenesulfinate aqueous solution; and S2, adding a zincchloride aqueous solution into the benzenesulfinate aqueous solution obtained in the S1, carrying out a reaction, and stopping the reaction; and carrying out cooling, carrying out filtering, carryingout washing by using water and carrying out drying to obtain the target product zinc benzenesulfinate, wherein the reaction temperature in the S2 is 50-90 DEG C, and the reaction time is 60-120 min;and preferably, the reaction temperature in the S2 is 72-75 DEG C, and the reaction time is 80-100 min. The synthetic method provided by the invention has the advantages of simple process steps, no use of organic solvents, no pollution, safety, environmental protection, a high yield, simple operation, raw materials convenient and easy to obtain, and low price; and the method is a synthetic route suitable for large-scale industrial production.
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Paragraph 0038-0090

(2020/01/12)

Synthesis of β-ketosulfone derivatives as new non-cytotoxic urease inhibitors in vitro
Background: Peptic ulcer and urolithiasis are largely due to infection caused by urease-producing bacteria. Therefore, the discovery of urease inhibitors is an important area of medicinal chemistry research. Objective: The main aim of the work was to identify novel urease inhibitors with no cytotoxicity. Method: During the current study, a series of β-ketosulfones 1-26 was synthesized in two steps and evaluated for their in vitro urease inhibition potential. Results: Out of twenty-six compounds, seventeen have shown good to significant urease inhibitory activity with IC50 values ranging between 49.93-351.46 μM, in comparison to standard thiourea (IC50 = 21 ± 0.11 μM). Moreover, all compounds found to be non-cytotoxic against normal 3T3 cell line. Conclusion: This study has identified β-ketosulfones as novel and non-cytotoxic urease inhibitors.
Iqbal Choudhary, M.,Iqbal, Sarosh,Khan, Ajmal,Khan, Khalid Mohammed,Kiran, Shumaila,Nazir, Rashid,Perveen, Shahnaz
p. 244 - 255
(2020/03/10)

Alkene: Versus alkyne reactivity in unactivated 1,6-enynes: Regio-And chemoselective radical cyclization with chalcogens under metal-And oxidant-free conditions
Herein, we have developed metal and oxidant-free visible light-promoted alkene vs. alkyne regio-And chemoselective radical cascade cyclization of electronically unbiased 1,6-enynes with chalcogens to synthesize substituted pyrrolidines bearing chalcogens. The reaction generated three new bonds, namely, C-SO2, C-C, and C-Se under extremely mild conditions. Furthermore, we achieved regio-And chemoselective mono-addition of aromatic thiophenols with unactivated 1,6-enynes. The key features of this protocol are broad substrate scope, environment-friendly conditions, operational simplicity, atom economy, and amenability to gram-scale synthesis. The mechanistic studies corroborate that the reaction proceeds via a radical pathway.
Kudale, Vishal Suresh,Li, Jing,Mutra, Mohana Reddy,Tsai, Wu-Hsun,Wang, Jeh-Jeng
supporting information
p. 2288 - 2300
(2020/04/21)

Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives
A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.
Wang, Fei,Liu, Bo-Xi,Rao, Weidong,Wang, Shun-Yi
supporting information
p. 6600 - 6604
(2020/09/02)

Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position
An efficient and convenient protocol for the direct sulfonylation of BODIPY dyes with sodium sulfinates via a radical process is described for the first time. This transformation presented wide substrate scope and high regioselectivity, providing a series of α-sulfonylated BODIPYs. Meaningfully, the sulfonyl group, as a good leaving group, allowed the facile introduction of a variety of functionalities on the BODIPY core. Moreover, a 2,4-dinitrobenzenesulfonyl (DBS) group substituted BODIPY showed dramatically quenched fluorescence via the photoinduced electron transfer (PET) pathway, and was demonstrated as a new fluorescent probe for selective biothiol detection. This journal is
Lv, Fan,Guo, Xing,Wu, Hao,Li, Heng,Tang, Bing,Yu, Changjiang,Hao, Erhong,Jiao, Lijuan
supporting information
p. 15577 - 15580
(2020/12/30)

A Facile Synthesis of 3-(Arylthio)imidazo[1,2-a]pyridin-2(3H)-ones from 2-Aminopyridinium Bromides and Sodium Arenesulfinates
A simple and convenient method has been developed for the synthesis of 3-(arylthio)imidazo[1,2-a]pyridin-2(3H)-ones through a catalyst-free reaction of 2-aminopyridinium bromides with sodium arenesulfinates. A variety of 3-(arylthio)imidazo[1,2-a]pyridin-2(3H)-ones were obtained in moderate to excellent (33–85 %) yields. The developed protocol is operationally simple, exhibits a broad substrate scope with a wide range of functional groups, and is amenable for gram-scale synthesis.
Kumar, Anil,Rangan, Krishnan,Saroj
p. 7015 - 7022
(2020/12/01)

A Convenient Synthesis of Sulfones via Light Promoted Coupling of Sodium Sulfinates and Aryl Halides
A convenient and e?cient synthesis of sulfones from sulfinates and aryl halides was developed. The reaction occurred under UV irradiation without transition metal catalyst or photocatalyst. A radical pathway via single-electron transfer (SET) of electron donor-acceptor (EDA) complex was proposed based on UV-vis spectroscopy, radical inhibiting and trapping experiments. (Figure presented.).
Chen, Lei,Liang, Jie,Chen, Zhen-yu,Chen, Jie,Yan, Ming,Zhang, Xue-jing
supporting information
p. 956 - 960
(2019/01/25)

Copper-Catalyzed Enantioselective Construction of Tertiary Propargylic Sulfones
Tertiary propargylic sulfones are of significant importance in organic synthesis and medicinal chemistry, but to date no general asymmetric synthesis approach has been developed. We disclose a versatile copper-catalyzed sulfonylation of propargylic cyclic carbonates using sodium sulfinates that allows the construction of propargylic sulfones featuring elusive quaternary stereocenters. This method provides the first successful example of such an enantioselective propargylic sulfonylation, features high asymmetric induction, wide functional group tolerance, and scalability, and enables attractive product diversification.
Gómez, José Enrique,Cristòfol, àlex,Kleij, Arjan W.
supporting information
p. 3903 - 3907
(2019/02/24)

Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates
A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.
Liu, Saiwen,Chen, Ru,Zhang, Jin
(2019/05/02)

SUBSTITUTED PHENYL SULFONYL PHENYL TRIAZOLE THIONES AND USES THEREOF
The present disclosure relates to substituted phenyl sulfonyl phenyl triazole thiones, pharmaceutical compositions containing them, and methods of using them.
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Paragraph 0178-0179

(2019/05/22)

Switchable regioselection of C-H thiolation of indoles using different TMS counterions
A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.
Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
p. 11864 - 11867
(2019/10/11)

Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates
Copper-catalyzed difunctionalization of 2-vinylbenzoic acids with sodium sulfinates to construct substituted lactones has been realized. This protocol employs inexpensive CuCl2 as the catalyst, di-tert-butyl peroxide or O2 as the terminal oxidant, and readily available sodium sulfinates as sulfonylation reagents. High functional group tolerance and excellent yields were demonstrated by the efficient preparation of a wide range of γ-sulfonylated phthalides.
Xiong, Yan-Shi,Zhang, Bin,Yu, Yang,Weng, Jiang,Lu, Gui
p. 13465 - 13472
(2019/10/16)

Regio- and Enantioselective Preparation of Chiral Allylic Sulfones Featuring Elusive Quaternary Stereocenters
We describe here the first general asymmetric synthesis of sterically encumbered α,α-disubstituted allylic sulfones via Pd-catalyzed allylic substitution. The design and application of a new and highly efficient phosphoramidite ligand (L10) proved to be crucial, and a wide variety of challenging allylic sulfones featuring quaternary stereocenters could be obtained in good yields and with good to excellent levels of regio- and enantioselectivities under attractive process conditions. The developed methodology employs easily accessible chemical feedstock including racemic allylic precursors and sodium sulfinates. The utility of the method is further demonstrated by the synthesis of the sesquiterpene (?)-Agelasidine A.
Cai, Aijie,Kleij, Arjan W.
supporting information
p. 14944 - 14949
(2019/11/05)

TRI-SUBSTITUTED ARYL AND HETEROARYL DERIVATIVES AS MODULATORS OF PI3-KINASE AND AUTOPHAGY PATHWAYS
The present disclosure relates to tri-substituted aryl and heteroaryl derivatives, pharmaceutical compositions containing them, and methods of using them, including methods for modulating autophagy or preventing, reversing, slowing or inhibiting the PI3K-AKT-MTOR pathway, and methods of treating diseases that are associated with autophagy or the PI3K-AKT-MTOR pathway.
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Paragraph 0209; 0210

(2019/11/04)

MORPHOLINE DERIVATES AS INHIBITORS OF VPS34
The present disclosure relates to thiazole- or diathiazole- substituted aryl and heteroaryl compounds (I), pharmaceutical compositions containing them, and methods of using them, including treatment of disorders or disease related to regulation of the Vps34/ PI3K III signaling pathway.
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Paragraph 0145

(2019/11/04)

METHOD OF TREATING A CONDITION ASSOCIATED WITH NEURODEGENERATION USING INHIBITORS OF OAT3
The present disclosure relates to therapeutic agents that may be useful in treatment and prophylaxis of neurodegenerative disorders and/or neural inflammation.
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Paragraph 0278-0279

(2020/01/11)

Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions
An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.
Liu, Yanan,Xie, Peizhong,Sun, Zuolian,Wo, Xiangyang,Gao, Cuiqing,Fu, Weishan,Loh, Teck-Peng
supporting information
p. 5353 - 5356
(2018/09/13)

Design, synthesis and biological evaluation of novel 2-sulfonylindoles as potential anti-inflammatory therapeutic agents for treatment of acute lung injury
Acute lung injury (ALI) is primarily driven by inflammation that severely impacts lung function. Novel 2-sulfonylindoles were recently shown to exhibit anti-inflammatory activity through the inhibition of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) production. Here, we synthesized 31 compounds which contained 2-sulfonylindole structure. The compounds 8a, 9g, 9h and 9k exhibited dose-dependent anti-inflammatory activity in vitro. Structural-activity relationship analysis revealed that the introduction of sulfonyl group in indole nucleus may be successful to obtain new anti-inflammatory structures and leads. The compounds 9h and 9k also decreased liposaccharide (LPS)-induced IL-6, IL-1β and vascular cell adhesion molecule-1 (VCAM-1) mRNA expression, both in vitro and in an in vivo model of ALI. Furthermore, the compounds 9h and 9k at a high dose (20 mg/kg) significantly protected against LPS-induced ALI in mice. These results show that compounds 9h and 9k could be a promising lead structure for the treatment of ALI.
Xia, Qinqin,Bao, Xiaodong,Sun, Chuchu,Wu, Di,Rong, Xiaona,Liu, Zhiguo,Gu, Yugui,Zhou, Jianmin,Liang, Guang
p. 120 - 132
(2018/10/21)

Fe-based metal-organic frameworks for the synthesis of N-arylsulfonamides via the reactions of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes in water
A newly developed chemoselective reaction of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes has been disclosed. The chemistry, in which non-toxic water and recyclable iron-based metal-organic frameworks are employed as the solvent and catalyst, respectively, provides an efficient approach for the generation of N-arylsulfonamides, which are widely present in biologically active compounds and drugs, rendering this methodology attractive to both synthetic and medicinal chemistry.
Li, Xinxin,Chen, Fei,Lu, Guo-Ping
supporting information
p. 4226 - 4230
(2018/10/26)

A radical cyclization cascade of 2-alkynylbenzonitriles with sodium arylsulfinates
A convenient radical cyclization cascade procedure for the construction of sulfonated indenones from 2-alkynylbenzonitriles and sodium arylsulfinates has been explored under mild reaction conditions. The present methodology offers a low-cost and operationally straightforward approach to synthesizing various sulfonated indenones in moderate to good yields by simple use of cheap sodium persulfate as an oxidant and environmentally benign water as a co-solvent.
Zhou, Bang,Chen, Wenqi,Yang, Yuzhong,Yang, Yuan,Deng, Guobo,Liang, Yun
supporting information
p. 7959 - 7963
(2018/11/21)

Iodine/TBHP-Promoted One-Pot Deoxygenation and Direct 2-Sulfonylation of Quinoline N-Oxides with Sodium Sulfinates: Facile and Regioselective Synthesis of 2-Sulfonylquinolines
A highly efficient iodine/TBHP-mediated one-pot deoxygenative and regioselective 2-sulfonylation of quinoline N-oxides with sodium sulfinate salts has been developed. This metal-, base-, and phosphorus-free protocol employs readily accessible and easy-to-handle reagents and can be conveniently carried out at room temperature under mild conditions, providing an alternative access to a series of 2-sulfonylquinolines and other related heteroaryl sulfone products in moderate-to-excellent yields within a short reaction time.
Sumunnee, Ladawan,Buathongjan, Chonchanok,Pimpasri, Chaleena,Yotphan, Sirilata
supporting information
p. 1025 - 1032
(2017/02/15)

Generation of trifluoromethyl thiolsulphonate through one-pot reaction of sulfonyl chloride and trifluoromethanesulfanylamides
A novel and efficient tandem reaction of sulfonyl chloride and trifluoromethylsulfanylamide is described here for the synthesis of various trifluoromethyl thiolsulphonates with a broad functional group tolerance. In the process, it is believed that sulfinate generated from sulfonyl chloride is a critical intermediate and the additive 4-methylbenzenesulfonic acid (p-TsOH) facilitates the formation of “CF3S+”. Electrophilic trifluoromethylthiolation of in situ generated sulfinate and “CF3S+” provides the final products.
Li, Yuewen,Qiu, Guanyinsheng,Wang, Hailong,Sheng, Jie
supporting information
p. 690 - 693
(2017/01/28)

Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent
A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of sulfone-substituted isoxazolines in good yields.
Wang, Li-Jing,Chen, Manman,Qi, Lin,Xu, Zhidong,Li, Wei
supporting information
p. 2056 - 2059
(2017/02/15)

QUINOLINE COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO THE MODULATION OF THE SEROTONIN 5-HT6 RECEPTOR
The present invention relates to quinoline compounds of formula I wherein the variables are defined as in the claims and the description. The invention further relates to a pharmaceutical composition containing such compounds, to their use as modulators of the 5-HT6 receptor, their use for preparing a medicament for the prevention or treatment of conditions and disorders which respond to the modulation of the 5-HT6 receptor, and to methods for preventing or treating conditions and disorders which respond to the modulation of the 5-HT6 receptor.
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Paragraph 0354

(2017/09/23)

Method for preparing aryl sulfinate
The invention provides a method for preparing an aryl sulfinate compound through the reaction of diaryl iodonium salt and sodium formaldehyde sulfoxylate.At room temperature, the diaryl iodonium salt reacts with the sodium formaldehyde sulfoxylate for 10-120 minutes to generate the corresponding aryl sulfinate compound.The method has the advantages that the reaction conditions are mild, the used reagents re easy to obtain, the application range of a substrate is wide, operation is simple, reaction is quick, and the like.
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Paragraph 0016

(2016/10/08)

Iron-catalyzed synthesis of arylsulfinates through radical coupling reaction
A novel strategy for installation of a sulfonyl fragment into arenes has been accomplished via an iron-catalyzed radical coupling reaction. Arene radicals derived from diaryliodoniums via single electron transfer reaction combine with sulfoxylate anion radicals readily generated from commercially available rongalite (HOCH2SO2Na·2H2O) to afford arylsulfinates efficiently at room temperature. In this protocol, a broad range of functional groups are tolerated to give products in good yields.
Zhang, Weixi,Luo, Meiming
p. 2980 - 2983
(2016/02/19)

Synthesis of sodium aryl sulfinates from aryl bromides employing 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) as a bench-stable, gas-free alternative to SO2
A convenient two-step protocol for the synthesis of sodium aryl sulfinates from aryl bromides and the SO2 surrogate 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) has been developed. A wide range of aryl bromides with respect to electronic properties were employed to give the corresponding sodium arylsulfinates in good to excellent yields. The protocol is especially efficient for electron poor aryl bromides which are often difficult to prepare using existing methods.
Skillinghaug, Bobo,Rydfjord, Jonas,Odell, Luke R.
supporting information
p. 533 - 536
(2016/01/20)

Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate
An unexpected Cu-catalyzed deoxygenative C2-sulfonylation reaction of quinoline N-oxides in the presence of radical initiator K2S2O8 was developed that used sodium sulfinate as a sulfonyl coupling partner. The mechanism studies indicate that the reaction proceeds via Minisci-like radical coupling step to give sulfonylated quinoline with good chemical yields.
Du, Bingnan,Qian, Ping,Wang, Yang,Mei, Haibo,Han, Jianlin,Pan, Yi
supporting information
p. 4144 - 4147
(2016/08/30)

(E)-Specific direct Julia-olefination of aryl alcohols without extra reducing agents promoted by bases
An unprecedented base-promoted direct olefination of aryl alcohols with sulfones via a Julia-type reaction has been described. No extra reductants are needed for Julia reaction since alcohols work as double sources of aldehydes and the hydride. Generally high yields were given for both terminal and highly (E)-selective internal olefins.
Yao, Chuan-Zhi,Li, Qiang-Qiang,Wang, Mei-Mei,Ning, Xiao-Shan,Kang, Yan-Biao
supporting information
p. 7729 - 7732
(2015/05/12)

Visible Light-Mediated Metal-Free Synthesis of Vinyl Sulfones from Aryl Sulfinates
Visible light and eosin Y catalyze the synthesis of vinyl sulfones from aryl sulfinates and alkenes by a photoredox process. The reaction scope is broad in aryl sulfinates and alkenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable vinyl sulfones.
Meyer, Andreas Uwe,J?ger, Stefanie,Prasad Hari, Durga,K?nig, Burkhard
supporting information
p. 2050 - 2054
(2015/06/23)

Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies
A fast and efficient protocol for the palladium(II)-catalyzed production of aryl ketones from sodium arylsulfinates and various organic nitriles under controlled microwave irradiation has been developed. The wide scope of the reaction has been demonstrated by combining 14 sodium arylsulfinates and 21 nitriles to give 55 examples of aryl ketones. One additional example illustrated that, through the choice of the nitrile reactant, benzofurans are also accessible. The reaction mechanism was investigated by electrospray ionization mass spectrometry and DFT calculations. The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The palladium(II) intermediates detected by ESI-MS and the DFT calculations provide a detailed understanding of the catalytic cycle. (Figure Presented).
Skillinghaug, Bobo,Sk?ld, Christian,Rydfjord, Jonas,Svensson, Fredrik,Behrends, Malte,S?vmarker, Jonas,Sj?berg, Per J. R.,Larhed, Mats
p. 12018 - 12032
(2015/01/16)

Copper-catalysed coupling of aryl tosylates with sodium arylsulfinates
Diaryl sulfones derivatives were easily synthesised from aryl tosylates and sodium arylsulfinates in high yields using [Cu(CH3CN)4]PF6 as catalyst. The transformation is efficient, simple and the starting materials are readily available.
Wang, Chunjie,Zhang, Hui,Li, Zhiwei,Wang, Ziyun
p. 639 - 642
(2015/02/02)

First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates
The first example of palladium-catalyzed protocol for the denitrated coupling of nitroarenes with sulfinates was developed, achieving aryl and heterocyclic sulfones in moderate to excellent yields. The cyclopalladated ferrocenylimine (I) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol %). The efficiency of this reaction was demonstrated by compatibility with a wide range of groups. Thus, the method represents a simple and facile procedure to access aryl and heterocyclic sulfones.
Tian, Heng,Cao, Aijuan,Qiao, Lijun,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
supporting information
p. 9107 - 9112
(2015/03/05)

Reactivity of sodium arenesulfinates in the substitution reaction to γ-functionalized allyl bromides
The kinetics of nucleophilic bimolecular substitution reactions of γ-functionalized allyl bromides with non-substituted and p-substituted sodium arenesulfinates has been studied. Both the structure of allyl bromides and nucleophilicity of arenesulfinate ions exerted a significant effect on the values of the kinetic parameters such as the second-order rate constants k, activation energy EA, and changes in the entropy ΔS≠, enthalpy ΔH≠, and free energy ΔG≠ of the formation of the activated complex from reactants. Based on the evaluation of kinetic parameters, the reactants could be arranged, according to their decreasing reactivity in the SN2-reactions as follows: p-toluenesulfinate ion > benzenesulfinate ion> p-chlorobenzenesulfinate ion and 4-bromo-2- butenenitrile> 1,3-dibromopropene, respectively. Comparison was also made between the kinetic data obtained and some delocalization reactivity indexes for both the substrates and nucleophiles. The enthalpy-entropy compensation effect was observed for the reactions of sodium arenesulfinates with γ-functionalized allyl bromides. Copyright
Khamis, Galina,Stoeva, Stoyanka,Aleksiev, Dimitar
supporting information; experimental part
p. 461 - 467
(2011/08/06)

Rapid synthesis of sulfone derivatives as potential anti-infectious agents
An original one-pot microwave reaction was developed for the synthesis of sulfone derivatives as new potent antimicrobial agents. This eco-friendly methodology conducted in 30 min led to desired products with good yields. The sulfones (4a and 4b) were obtained via the reaction of 3a with the corresponding halo-derivatives in the presence of sodium hydride. All compounds were tested for their antibacterial and antifungal activities against four bacterial strains (two gram positive, and two gram negative ones) and two yeasts. The disk diffusion method has shown an interesting antibacterial activity for seven compounds (3b-g and 4b) against Staphylococcus aureus. Among these seven compounds, five derivatives (3b-e and 3g) showed activity against Candida tropicalis.
Curti,Laget,Carle, A. Ortiz,Gellis,Vanelle
p. 880 - 884
(2008/02/12)

PROCESS FOR PRODUCING 3-CHLOROMETHYL-3-CEPHEM DERIVATIVE
An industrially advantageous process for producing 3-chloromethyl-3-cephem derivative crystals. The process for 3-chloromethyl-3-cephem derivative production comprises: a first step in which a thiazolineazetidinone derivative (1) is reacted with a sulfonyl halide (2) in the presence of an acid in a solvent to obtain an azetidinone derivative (3); a second step in which the azetidinone derivative (3) is reacted with a chlorinating agent in an organic solvent to obtain a chlorinated azetidinone derivative (4); and a third step in which the chlorinated azetidinone derivative (4) is reacted with an alcoholate (5) at a pH of 8 or lower in a solvent comprising an alcohol and an ether and a 3-chloromethyl-3-cephem derivative (6) is recovered in the form of crystals.
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Page/Page column 16-19

(2008/06/13)

Isothiazolecarboxylic acid derivatives and their use as microbicides
Novel isothiazolecarboxylic acid derivatives of the formula (I), in which A, Q, Z and k have the meanings mentioned in the specification, processes for the preparation of the new compounds and their use as microbicides.
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(2008/06/13)

Method of producing alkali metal benzenesulfinates
A method of producing alkali metal benzenesulfinates having the general formula of STR1 wherein M represents Na or K, which comprises: reacting nitrophenylphenyl sulfones having the general formula of STR2 wherein n is an integer of 1 or 2, with alkali metal thiophenolates having the general formula of STR3 in solvents. The reaction produces also nitrophenylphenyl sulfides as by-products in equimolar amounts to the alkali metal benzenesulfinates, and the oxidation of the sulfides provides the starting nitrophenylphenyl sulfones. A method of producing the nitrophenylphenyl sulfones is also provided wherein the sulfides are oxidized with hydrogen peroxide in the presence both of water-soluble tungstates or molybdates and of phase transfer catalysts in a two-phase heterogeneous solvent.
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(2008/06/13)

Generation of Sulfenate Salts via Ipso-substitution of Azaheterocyclic Sulfoxides. First Preparation and Characterization of Sodium 2-Pyridinesulfenate
2-Alkyl- or 2-aryl-sulfinylpyridine N-oxides undergo ipsosubstitution reaction with sodium ethoxide to afford sodium sulfenates which were converted soon to the corresponding sulfinates upon contact with oxygen.Sodium 2-pyridinesulfenate was prepared and characterized by FT-IR as the first example of stable sulfenate.
Furukawa, Naomichi,Konno, Yasuo,Tsuruoka, Masayuki,Fujihara, Hisashi,Ogawa, Satoshi
p. 1501 - 1504
(2007/10/02)

A CONVENIENT PREPARATION OF SULFINIC ACIDS BY THE REACTION OF 2-SULFONYLPYRIDINES AND THEIR N-OXIDES WITH NUCLEOPHILES
Ipso-substitution reaction of 2-sulfonylpyridines and their N-oxides with alkoxide or thiolate anion afforded the sodium salts of sulfinic acids together with the corresponding substitution product in high yields.This procedure becomes a convenient and versatile method for preparation of various sulfinic acids.
Furukawa, Naomichi,Tsuruoka, Masayuki,Fujihara, Hisashi
p. 3019 - 3022
(2007/10/02)