cas 1939-99-7, alpha-Toluenesulfonyl chloride

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Scott et al.
p. 1165,1167
(1955)
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TAPC-promoted synthesis of sulfonyl chlorides from sulfonic acids
A novel and efficient method is described for the preparation of sulfonyl chlorides from sulfonic acids using TAPC as chlorinating agent. Mild reaction conditions, shorter reaction times, high efficiencies, cost-effectiveness, and facile isolation of the desired products make the present methodology a practical alternative and will provide a valuable synthetic tool for various pharmaceutical applications. Georg Thieme Verlag Stuttgart · New York.
Bahrami, Kiumars
p. 2671 - 2674
(2011)
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An efficient method for the preparation of sulfonyl chlorides: Reaction of disulfides or thiols with sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals
The reaction of disulfides or thiols with sodium hypochlorite pentahydrate in acetic acid efficiently provided the corresponding sulfonyl chlorides in high yields.
Okada, Tomohide,Matsumuro, Hiroaki,Iwai, Toshiaki,Kitagawa, Saori,Yamazaki, Kento,Akiyama, Tomomi,Asawa, Tomotake,Sugiyama, Yukihiro,Kimura, Yoshikazu,Kirihara, Masayuki
p. 185 - 187
(2015)
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Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst
Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.
Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias
supporting information
p. 20543 - 20550
(2021/08/12)

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
(2021/09/20)

Design, synthesis and biological evaluation of novel N-sulfonylamidine-based derivatives as c-Met inhibitors via Cu-catalyzed three-component reaction
In our continuing efforts to develop novel c-Met inhibitors as potential anticancer candidates, a series of new N-sulfonylamidine derivatives were designed, synthesized via Cu-catalyzed multicomponent reaction (MCR) as the key step, and evaluated for their in vitro biological activities against c-Met kinase and four cancer cell lines (A549, HT-29, MKN-45 and MDA-MB-231). Most of the target compounds showed moderate to significant potency at both the enzyme-based and cell-based assay and possessed selectivity for A549 and HT-29 cancer cell lines. The preliminary SAR studies demonstrated that compound 26af (c-Met IC50 = 2.89 nM) was the most promising compound compared with the positive foretinib, which exhibited the remarkable antiproliferative activities, with IC50 values ranging from 0.28 to 0.72 μM. Mechanistic studies of 26af showed the anticancer activity was closely related to the blocking phosphorylation of c-Met, leading to cell cycle arresting at G2/M phase and apoptosis of A549 cells by a concentration-dependent manner. The promising compound 26af was further identified as a relatively selective inhibitor of c-Met kinase, which also possessed an acceptable safety profile and favorable pharmacokinetic properties in BALB/c mouse. The favorable drug-likeness of 26af suggested that N-sulfonylamidines may be used as a promising scaffold for antitumor drug development. Additionally, the docking study and molecular dynamics simulations of 26af revealed a common mode of interaction with the binding site of c-Met. These positive results indicated that compound 26af is a potential anti-cancer candidate for clinical trials, and deserves further development as a selective c-Met inhibitor.
Fang, Sen-Biao,Li, Hui-Jing,Nan, Xiang,Wu, Rui,Wu, Yan-Chao,Zhang, Jing,Zhang, Zhi-Zhou
(2020/06/04)

Design, synthesis and evaluation of sulfonylurea-containing 4-phenoxyquinolines as highly selective c-Met kinase inhibitors
Deregulation of receptor tyrosine kinase c-Met has been reported in human cancers and is considered as an attractive target for small molecule drug discovery. In this study, a series of 4-phenoxyquinoline derivatives bearing sulfonylurea moiety were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against tested four cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant potency as compared with foretinib, with the most promising compound 13x (c-Met kinase IC50 = 1.98 nM) demonstrated relatively good selectivity versus 10 other tyrosine kinases and remarkable cytotoxicities against HT460, MKN-45, HT-29 and MDA-MB-231 with IC50 values of 0.055 μM, 0.064 μM, 0.16 μM and 0.49 μM, respectively. The preliminary structure activity relationships indicated that a sulfonylurea moiety as linker as well as mono-EGWs (such as R1 = 4-F) on the terminal phenyl rings contributed to the antitumor activity.
Nan, Xiang,Jiang, Yi-Fan,Li, Hui-Jing,Wang, Jun-Hu,Wu, Yan-Chao
supporting information
p. 2801 - 2812
(2019/05/15)

High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides
In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.
Sohrabnezhad, Samira,Bahrami, Kiumars,Hakimpoor, Farahman
p. 256 - 264
(2019/02/06)

Template-Assisted meta-C?H Alkylation and Alkenylation of Arenes
To expand the scope of meta-functionalization, a pyrimidine-based template effective for the formation of β-aryl aldehydes and ketones, using allyl alcohols, by meta-C?H activation of benzylsulfonyl esters is described. In addition, α,β-unsaturated aldehydes were generated by in situ olefination and deprotection of allyl benzyl ethers. These new functionalizations at the meta-position of an arene have also been successfully implemented in benzylphosphonate, phenethyl carbonyl, and phenethylsulfonyl ester scaffolds. Key to these successful new functionalizations is the creation of an electropositive palladium center by accepting the electron cloud from the metal to the energetically low-lying π-orbitals of pyrimidine ring, and it favors coordination of allyl alcohol to the metal center.
Bag, Sukdev,Jayarajan, Ramasamy,Mondal, Rahul,Maiti, Debabrata
supporting information
p. 3182 - 3186
(2017/03/17)

Rhodium-Catalyzed meta-C?H Functionalization of Arenes
Rhodium-catalyzed ortho-C?H functionalization is well known in the literature. Described herein is the Xphos-supported rhodium catalysis of meta-C?H olefination of benzylsulfonic acid and phenyl acetic acid frameworks with the assistance of a para-methoxy-substituted cyano phenol as the directing group. Complete mono-selectivity is observed for both scaffolds. A wide range of olefins and functional groups attached to arene are tolerated in this protocol.
Bera, Milan,Agasti, Soumitra,Chowdhury, Rajdip,Mondal, Rahul,Pal, Debasis,Maiti, Debabrata
supporting information
p. 5272 - 5276
(2017/04/27)

Palladium-Catalyzed Remote meta-Selective C-H Bond Silylation and Germanylation
Selective meta-C-H activation of arenes to date has met with a limited number of functionalizations. Expanding the horizon of meta-C-H functionalization, herein we disclose an unprecedented meta-silylation and -germanylation protocol by employing a simple nitrile-based directing template. Longer linkers between the target site and the directing template were successfully explored for meta-silylation (sp2-? and sp2-ζ). Additionally, synthetic utility was demonstrated with several postsynthetic elaborations and with a formal synthesis of TAC101, a promising drug for the treatment of lung cancer.
Modak, Atanu,Patra, Tuhin,Chowdhury, Rajdip,Raul, Suman,Maiti, Debabrata
supporting information
p. 2418 - 2423
(2017/07/17)

Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH
A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.
Silva-Cuevas, Carolina,Perez-Arrieta, Carlos,Polindara-García, Luis A.,Lujan-Montelongo, J. Armando
supporting information
p. 2244 - 2247
(2017/05/16)

Photocatalytic Radical Alkylation of Electrophilic Olefins by Benzylic and Alkylic Zinc-Sulfinates
Alkyl radicals are obtained by photocatalytic oxidation of readily prepared or commercially available zinc sulfinates. The convenient benzylation and alkylation of a variety of electron-poor olefins triggered by the iridium(III) complex 6 Ir[dF(CF3)ppy]2(dtbbpy)PF6 as photocatalyst is described. Moreover, it is shown that zinc sulfinates can be used for facile nonradical sulfonylation reactions with highly electrophilic Michael acceptors.
Gualandi, Andrea,Mazzarella, Daniele,Ortega-Martínez, Aitor,Mengozzi, Luca,Calcinelli, Fabio,Matteucci, Elia,Monti, Filippo,Armaroli, Nicola,Sambri, Letizia,Cozzi, Pier Giorgio
p. 5357 - 5362
(2017/08/17)

Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides
A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.
Yang, Zhanhui,Xu, Wei,Wu, Qiuyue,Xu, Jiaxi
p. 3051 - 3057
(2016/04/26)

A α-pinene derivatives and its preparation method and application (by machine translation)
This invention has offered a kind of α-pinene derivatives, the derivatives of formula I such as a structural formula shown in formula II. Said α-pinene derivatives by the reduction, the organic acid ester and the like introduced into the α-pinene in the molecule skeleton to obtain new derivatives. Research shows that in vitro anti-tumor activity, the present invention provides the α-pinene derivatives to liver cancer cells has significant inhibition function, as the preparation of anti-tumor compound or its pharmaceutically acceptable salt, hydrate, solvate or prodrug, has good application prospect. Type I ;? ? ? Type II. (by machine translation)
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Paragraph 0175; 0176

(2016/10/09)

METHOD FOR PRODUCING SULFONYL CHLORIDE COMPOUNDS
PROBLEM TO BE SOLVED: To provide a production method which enables safe and simple production of sulfonyl chloride compounds in high yields, which are useful as intermediates for medicines, agrochemicals, functional materials, and the like. SOLUTION: Provided is a method for producing sulfonyl chloride compounds comprising oxidation of thiols or disulfides in the presence of an oxidizing agent to produce sulfonyl chloride compounds. As the oxidizing agent is used sodium hypochlorite, and the reaction is performed with the pH of the reaction system adjusted to a neutral or acidic value of pH 7 or less. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0028; 0030

(2018/11/22)

Tert -Butyl Hypochlorite Mediated Oxidative Chlorination of S -Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides
Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.
Qiu, Kui,Wang, Rennan
p. 3186 - 3190
(2015/10/19)

Palladium(II)-Catalyzed meta-C-H Olefination: Constructing Multisubstituted Arenes through Homo-Diolefination and Sequential Hetero-Diolefination
Divinylbenzene derivatives represent an important class of molecular building blocks in organic chemistry and materials science. Reported herein is the palladium-catalyzed synthesis of divinylbenzenes by meta-C-H olefination of sulfone-based arenes. Successful sequential olefinations in a position-selective manner provided a novel route for the synthesis of hetero-dialkenylated products, which are difficult to access using conventional methods. Additionally, 1,3,5-trialkenylated compounds can be generated upon successful removal of the directing group. Jockeying for position: Reported herein is the palladium-catalyzed synthesis of mono- and divinylbenzenes by meta-C-H olefination of benzyl sulfones. Successful sequential olefinations in a position-selective manner provided a novel route for the synthesis of hetero-dialkenylated products, which are difficult to access using conventional methods. DG=directing group.
Bera, Milan,Maji, Arun,Sahoo, Santosh K.,Maiti, Debabrata
supporting information
p. 8515 - 8519
(2015/11/27)

Preparation of alkanesulfonyl chlorides from s-alkyl isothiourea salts via n-chlorosuccinimide mediated oxidative chlorosulfonation
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Yang, Zhanhui,Xu, Jiaxi
p. 116 - 124
(2014/04/17)

Clean and economic synthesis of alkanesulfonyl chlorides from S-alkyl isothiourea salts via bleach oxidative chlorosulfonation
A simple procedure for clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is disclosed. This procedure is environment- and worker-friendly with the advantages of readily accessible materials and reagents, simple and safe operations, easy purification without chromatography, and affords high yields of up to 99%.
Yang, Zhanhui,Zhou, Bingnan,Xu, Jiaxi
p. 225 - 229
(2014/03/21)

Oxidation of disulfides with electrophilic halogenating reagents: Concise methods for preparation of thiosulfonates and sulfonyl halides
The reaction of aromatic or benzylic disulfides with 2.5 equiv of Selectfluor in acetonitrile/water (10:1) at room temperature efficiently produced the corresponding thiosulfonates. Conversely, the reaction of disulfides with 6.5 equiv of Selectfluor or thiosulfonates with 4.5 equiv of Selectfluor in refluxing acetonitrile/water (10:1) provided sulfonyl fluorides in high yields. Accufluor and FP-T300 are also effective in preparing sulfonyl fluorides from disulfides under the similar reaction conditions. Sulfonyl chlorides or sulfonyl bromides were effectively obtained from the reaction of disulfides with 6 equiv of either N-chlorosuccinimide or N-bromosuccinimide in acetonitrile/water (10:1) at room temperature. Some other electrophilic chlorinating or brominating reagents are also able to be used instead of N-chlorosuccinimide or N-bromosuccinimide for the syntheses of sulfonyl halides from disulfides. These reactions of disulfides with electrophilic halogenating reagents are convenient methods to prepare thiosulfonates and sulfonyl halides.
Kirihara, Masayuki,Naito, Sayuri,Nishimura, Yuki,Ishizuka, Yuki,Iwai, Toshiaki,Takeuchi, Haruka,Ogata, Tomomi,Hanai, Honoka,Kinoshita, Yukari,Kishida, Mari,Yamazaki, Kento,Noguchi, Takuya,Yamashoji, Shiro
p. 2464 - 2471
(2014/04/03)

Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation
A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.
Yang, Zhanhui,Xu, Jiaxi
p. 1675 - 1682
(2013/07/27)

Simple synthesis of sulfonyl chlorides from thiol precursors and derivatives by NaClO2-mediated oxidative chlorosulfonation
A simple method to synthesize diverse sulfonyl chlorides through NaClO 2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is presented. The approach features safe operation, environmental friendliness, convenient purification procedures, and delivers high yields of up to 96%. The procedure is also applicable to substrates such as thiols, disulfides, thioacetates, and xanthates. It is a versatile and convenient method for the synthesis of various sulfonyl chlorides from different thiol precursors and derivatives. Georg Thieme Verlag Stuttgart, New York.
Yang, Zhanhui,Zheng, Yongpeng,Xu, Jiaxi
p. 2165 - 2169
(2013/10/22)

Synthesis and receptor binding studies of novel 4,4-disubstituted arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as a new class of σ1 ligands
This study presents the synthesis and biological evaluation of a new series of arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as sigma receptor ligands. It was found that a number of halogen substituted sulfonamides display relatively high and low affinities to σ1 and σ2 receptors, respectively. The σ1 affinities and subtype selectivities of four piperidine derivatives were also found to be generally comparable to those of piperazine analogues. Compared to σ1-Rs compounds with n = 0 and 2, those with n = 1 proved to have optimal length of carbon chain by exhibiting higher affinities. Within this series, the 4-benzyl-1-(3-iodobenzylsulfonyl)piperidine sigma ligand was identified with 96-fold σ1/σ2 selectivity ratio (Kiσ1 = 0.96 ± 0.05 nM and K iσ2 = 91.8 ± 8.1 nM).
Sadeghzadeh, Masoud,Sheibani, Shahab,Ghandi, Mehdi,Daha, Fariba Johari,Amanlou, Massoud,Arjmand, Mohammad,Hasani Bozcheloie, Abolfazl
p. 488 - 497
(2013/07/27)

One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T
A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine-T (=N-chlorotosylamide=N-chloro-4- methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.
Maleki, Behrooz,Hemmati, Saba,Tayebee, Reza,Salemi, Sirous,Farokhzad, Yasaman,Baghayeri, Mehdi,Zonoz, Farrokhzad Mohammadi,Akbarzadeh, Elahe,Moradi, Rohollah,Entezari, Azam,Abdi, Mohammad Reza,Ashrafi, Samaneh Sedigh,Taimazi, Fereshteh,Hashemi, Majid
p. 2147 - 2151
(2013/12/04)

Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) as efficient reagents for the direct oxidative conversion of thiols and disulfides to sulfonyl chlorides
Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) were found to be mild and efficient reagents for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good-to-excellent yields through the oxidative chlorination. The overall process is simple and practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides. Copyright
Veisi, Hojat,Sedrpoushan, Alireza,Hemmati, Saba,Kordestani, Davood
experimental part
p. 769 - 775
(2012/06/30)

Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles
H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and di-sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. Georg Thieme Verlag Stuttgart · New York.
Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
experimental part
p. 316 - 322
(2012/03/26)

Convenient one-pot synthesis of sulfonamides from thiols and disulfides using 1,3-dichloro-5,5-dimethylhydantoin (DCH)
A convenient synthesis of sulfonamides from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with 1,3-dichloro-5,5-dimethylhydantoin (DCH) under Nbenzyl-trimethylammonium chloride and water. The sulfonyl chlorides are then further allowed to react with excess amine in the same reaction vessel.
Veisi, Hojat
experimental part
p. 383 - 386
(2012/04/23)

Synthesis of sulfonyl chlorides and thiosulfonates from H2O 2-TiCl4
A new method is described for the oxidative chlorination of thiols to sulfonyl chlorides using titanium tetrachloride in combination with the oxidant hydrogen peroxide. Direct conversion of thiols into their corresponding thiosulfonates is also reported. Good to excellent yields, short reaction times, high efficiencies, cost-effectiveness, and, facile isolation of the desired products make the present methodology a practical alternative.
Bahrami, Kiumars,Khodaei, Mohammad M.,Khaledian, Donya
experimental part
p. 354 - 358
(2012/01/19)

Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system
Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.
Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
supporting information; experimental part
p. 5095 - 5101
(2012/07/28)

Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide as efficient reagents to direct oxidative conversion of thiols and disulfide to sulfonyl chlorides
Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) (PCBS) and N,N,N',N'-Tetrachlorobenzene-1,3- disulfonamide (TCBDA) were found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through the oxidative chlorination. The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive, and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.
Veisi, Hojat,Ghorbani-Vaghei, Ramin,Mahmoodi, Jafar
experimental part
p. 3692 - 3695
(2012/01/11)

Diverse reactions of sulfonyl chlorides and cyclic imines
Although alkanesulfonyl chlorides react with linear imines to give rise to β-sultam derivatives, in this study, they were reacted with various cyclic imines, including 1-pyrroline, oxazoline, 5,6-dihydro-4H-oxazines and thiazines, 4,5-dihydro-3H-benzo[c]azepine, and 3,4-dihydroisoquinoline, to produce diverse products instead of β-sultam derivatives. The results indicate that alkanesulfonyl chlorides react with cyclic imines to generate N-alkanesulfonyl cyclic iminium ions, which are attacked by nucleophiles, such as water and chloride anion, in the reaction systems, affording addition products. The iminium intermediates cannot undergo a ring closure to form β-sultam derivatives. Arenesulfonyl chlorides showed similar behavior when they reacted with cyclic imines. The scope and limitation of the reaction between sulfonyl chlorides and imines were investigated. Copyright Taylor & Francis Group, LLC.
Liu, Jing,Hou, Shili,Xu, Jiaxi
experimental part
p. 2377 - 2391
(2012/04/04)

DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation
The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.
Woolven, Holly,Gonzalez-Rodriguez, Carlos,Marco, Isabel,Thompson, Amber L.,Willis, Michael C.
supporting information; experimental part
p. 4876 - 4878
(2011/12/05)

New synthesis of alkane- and arylsulfonyl chlorides by oxidation of thiols and disulfi des with chlorine dioxide
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Lezina,Rubtsova,Kuchin
experimental part
p. 1249 - 1251
(2011/12/01)

Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide
A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel. Georg Thieme Verlag Stuttgart - New York.
Veisi, Hojat,Ghorbani-Vaghei, Ramin,Hemmati, Saba,Mahmoodi, Jafar
experimental part
p. 2315 - 2320
(2011/10/13)

A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides
2,4-Dichloro-5,5-dimethylhydantoin (DCDMH) was found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through oxidative chlorination. The method is suitable for many types of sulfur substrates (thiols, disulfides, and benzylic sulfides). The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.
Pu, Yu-Ming,Christesen, Alan,Ku, Yi-Yin
supporting information; experimental part
p. 418 - 421
(2010/03/04)

A novel, practical synthesis of sulfonyl chlorides from thiol and disulfide derivatives
Hydrogen peroxide, in the presence of zirconium tetrachloride, is a very efficient reagent for the direct oxidative conversion of thiol and disulfide derivatives into the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Excellent yields, very short reaction times, mild reaction conditions, and the avoidance of harsh reagents are the main advantages of this method.
Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Soheilizad, Mehdi
experimental part
p. 2773 - 2776
(2010/02/28)

Direct conversion of thiols to sulfonyl chlorides and sulfonamides
(Chemical Equation Presented) H2O2 in combination with SOCl2 proved to be a highly reactive reagent for the direct oxidative conversion of thiol derivatives to the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Upon reaction with amines, the corresponding sulfonamides were obtained in excellent yields and in very short reaction times.
Bahrami, Kiumars,Khodaei, Mohammad M.,Soheilizad, Mehdi
supporting information; experimental part
p. 9287 - 9291
(2010/03/04)

Novel naphthalene-N-sulfonyl-D-glutamic acid derivatives as inhibitors of MurD, a key peptidoglycan biosynthesis enzyme
Mur ligases have essential roles in the biosynthesis of peptidoglycan, and they represent attractive targets for the design of novel antibacterials. MurD (UDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase) is the second enzyme in the series of Mur ligases, and it catalyzes the addition of D-glutamic acid (D-Glu) to the cytoplasmic intermediate UDP-N-acetylmuramoyl-L-alanine (UMA). Because of the high binding affinity of D-Glu toward MurD, we synthesized and biochemically evaluated a series of N-substituted D-Glu derivatives as potential inhibitors of MurD from E. coli, which allowed us to explore the structure-activity relationships. The substituted naphthalene-N-sulfonyl-D-Glu inhibitors, which were synthesized as potential transitionstate analogues, displayed IC50 values ranging from 80 to 600 μM. In addition, the high-resolution crystal structures of MurD in complex with four novel inhibitors revealed details of the binding mode of the inhibitors within the active site of MurD. Structure-activity relationships and cocrystal structures constitute an excellent starting point for further development of novel MurD inhibitors of this structural class.
Humljan, Jan,Kotnik, Miha,Contreras-Martel, Carlos,Blanot, Didier,Urleb, Uro?,Dessen, Andréa,?olmajer, Tom,Gobec, Stanislav
scheme or table
p. 7486 - 7494
(2009/11/30)

Sulfonyl chloride formation from thiol derivatives by N-chlorosuccinimide mediated oxidation
Oxidation of several thiol derivatives by a combination of N-chlorosuccinimide and dilute hydrochloric acid proceeded smoothly, affording the corresponding sulfonyl chlorides in good yield. Georg Thieme Verlag Stuttgart.
Nishiguchi, Atsuko,Maeda, Kazuhiro,Miki, Shokyo
p. 4131 - 4134
(2008/03/13)

N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing
A series of 11 N-sulfonyl homoserine lactones has been synthesised. Some of them were found to competitively inhibit the action of 3-oxohexanoyl-L- homoserine lactone, the natural inducer of bioluminescence in the bacterium Vibrio fischeri. Molecular modeling suggests a possible explanation based on the prevention of structural rearrangements necessary for the formation of the active dimer of LuxR.
Castang, Sandra,Chantegrel, Bernard,Deshayes, Christian,Dolmazon, René,Gouet, Patrice,Haser, Richard,Reverchon, Sylvie,Nasser, William,Hugouvieux-Cotte-Pattat, Nicole,Doutheau, Alain
p. 5145 - 5149
(2007/10/03)

Benzene-condensed heterocyclic derivatives and their uses
PCT No. PCT/JP96/00011 Sec. 371 Date Jun. 26, 1997 Sec. 102(e) Date Jun. 26, 1997 PCT Filed Jan. 8, 1996 PCT Pub. No. WO96/20925 PCT Pub. Date Jul. 11, 1996Novel compounds having strong TXA2 receptor antagonist activities and PGI2 receptor agonist activities, which are effective for therapy and prevention of diseases related to TXA2, are disclosed. The compound of the present invention is represented by the following formula (I). (wherein the meanings of the symbols in the formula are as described in the specification).
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(2008/06/13)

Solid-state organic reactions proceeding by pulverization: Oxidation and halogenation with iodosobenzene and inorganic solid-supports
Pulverization-activation method was employed to accelerate solid-state organic reactions. Crushing and grinding of solid mixtures of hydrogen halide-treated silica gels, iodosobenzene and organic substrates in the absence of a solvent brought about smooth and rapid reactions to give halogenated and/or oxidized products in good yields. Various sulfides were smoothly converted to sulfonyl chlorides in one step in excellent yields. The surface of silica gel activated by pulverization serves as a reaction field on which reagent molecules can effectively encounter with each other.
Sohmiya, Hajime,Kimura, Takahide,Fujita, Mitsue,Ando, Takashi
p. 13737 - 13750
(2007/10/03)

Convenient One-Pot Synthesis of Sulfonyl Chlorides from Thiols Using Sulfuryl Chloride and Metal Nitrate
Various sulfonyl chlorides were obtained in excellent yields by the reaction of alkyl and aryl thiols with sulfuryl chloride in the presence of metal nitrate under mild condition in aprotic solvents such as acetonitrile and N,N-dimethylformamide.
Park, Young Jun,Shin, Hyun Ho,Kim, Yong Hae
p. 1483 - 1486
(2007/10/02)

A new and facile synthesis of sulfonyl chlorides
Several benzenesulfonyl and arylmethanesulfonyl chlorides 2 are synthesized in excellent yields by the aqueous chlorination of aryl (or benzyl) methoxymethyl sulfides 1. Functionalized sulfides 1 d-g can be prepared easily from bromophenyl methoxymethyl sulfides 1b,c.
Kim,Ko,Kim
p. 1203 - 1204
(2007/10/02)

Novel One-Step Synthesis of Sulfonyl Chlorides from Sulfides with Iodosobenzene and Hydrogen Chloride-Treated Silica Gel
Alkyl and aryl benzyl sulfides were conveniently converted into the corresponding alkyl and aryl sulfonyl chlorides in high yields with a few minutes' pulverization of solid mixtures with iodosobenzene and hydrogen chloride-treated silica gel.
Sohmiya, Hajime,Kimura, Takahide,Fujita, Mitsue,Ando, Takashi
p. 891 - 892
(2007/10/02)

A new application of S,S-dialkyl dithiocarbonates. A convenient synthesis of alkanesulfonyl chlorides
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Barbero,Cadamuro,Degani,Fochi,Regondi
p. 957 - 958
(2007/10/02)

Intramolecular sulphonyl-amidomethylation. Part I. Cyclization of benzylsulphonamides
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Orazi,Corral,Bravo
p. 1701 - 1708
(2007/10/02)

The sulfohaloform reaction revisited and revised
A study of the aqueous chlorinolyses of a series of benzylic dithioacetals along with related α-chlorobenzylic sulfides is reported.These results require a modification of our previously proposed sulfohaloform reaction, so that thionium ion intermediates which have at least one alkyl group on sp2 carbon follow a different pathway.
Baum, James Clayton,Hardstaff, William Rayne,Langler, Richard Francis,Makkinje, Anthony
p. 1687 - 1691
(2007/10/02)

REACTION OF ARYLMETHANESULFONYL AND STYRYLMETHANESULFONYL CHLORIDES WITH TRIETHYLAMINE
A series of arylmethanesulfonyl chlorides were treated with triethylamine in THF to give stilbenes in excellent yields.Workup of the mixtures below 10 deg C permits isolation of stilbene episulfones which on warming decompose to yield the corresponding stilbenes stereospecifically.Application of the reaction to 9-fluorenylsulfonyl chloride affords bifluorenylidene, while trans-styrylmethanesulfonyl chloride gives 4,5-dihydro-4,5-diphenylthiepin 1,1-dioxide and 1,6-diphenylhexatriene.
Nakayama, Juzo,Tanuma, Mitsuru,Honda, Yoshiko,Hoshino, Masamatsu
p. 4553 - 4556
(2007/10/02)

Structure-activity studies on antihyperlipidemic N-benzoylsulfamates, N-benzylsulfamates, and benzylsulfonamides
A series of aryl substituted N-benzoyl- and N-benzylsulfamic acid sodium salts and benzylsulfonamide sodium salts have been prepared and examined for antihyperlipidemic activity in male CF1 mice at a dose level of 20 mg/kg/d ip for 16 d. These substances were also subjected to toxicological evaluation and chemical stability studies. In general, both series of sulfamates and sulfonamides significantly lowered serum cholesterol and triglyceride levels in mice. The compounds were nonmutagenic, showed no acute toxicity or impaired liver or kidney function in male mice, and were chemically stable both as the monohydrates and in aqueous solution over a pH range of 3.5-7.4. While both series of sulfamates and sulfonamides lowered serum cholesterol and triglyceride levels, the sulfamates were relatively more potent with regard to decreasing cholesterol levels, while the sulfonamides were more effective in lowering serum triglyceride levels in mice.
Wyrick,Hall,Dubey
p. 374 - 377
(2007/10/02)