- High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides
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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
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p. 256 - 264
(2019/02/06)
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- Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH
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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
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supporting information
p. 2244 - 2247
(2017/05/16)
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- Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions
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An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and "filtered" over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A "one-pot" protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.
- Jereb, Marjan,Hribernik, Luka
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supporting information
p. 2286 - 2295
(2017/07/24)
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- METHOD FOR PRODUCING SULFONYL CHLORIDE COMPOUNDS
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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)
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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
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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
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p. 185 - 187
(2015/02/19)
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- Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water
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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.
- Madabhushi, Sridhar,Jillella, Raveendra,Sriramoju, Vinodkumar,Singh, Rajpal
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supporting information
p. 3125 - 3131
(2014/06/10)
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- Oxidation of disulfides with electrophilic halogenating reagents: Concise methods for preparation of thiosulfonates and sulfonyl halides
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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
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p. 2464 - 2471
(2014/04/03)
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- One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, alcohols to bis(indolyl)methanes and synthesis of pyrroles catalyzed by N-chloro reagents
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A convenient synthesis of sulfonic esters from thiols and disulfides has been described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with Chloramin-T, tetra-butylammonium chloride (t-Bu4NCl) and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of bis(indolyl)methanes from alcohols using TCCA/KBr/wet-SiO2, and N-substituted pyrroles by reaction of hexane-2,5-dione with primary amines has been accomplished under mild condition with excellent yields.
- Veisi, Hojat,Ataee, Meral,Fatolahi, Leila,Lotfi, Shahram
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p. 111 - 117
(2013/07/26)
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- One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal-Knorr synthesis of pyrrole derivatives catalyzed by TCCA
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A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.
- Hemmati, Saba,Mojtahedi, Mohammad Majid,Abaee, Mohammad Saeed,Vafajoo, Zahra,Saremi, Shokufe Ghahri,Noroozi, Mohammad,Sedrpoushan, Alireza,Ataee, Meral
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p. 347 - 357
(2013/09/23)
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- Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) as efficient reagents for the direct oxidative conversion of thiols and disulfides to sulfonyl chlorides
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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
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experimental part
p. 769 - 775
(2012/06/30)
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- Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles
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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
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experimental part
p. 316 - 322
(2012/03/26)
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- Synthesis of sulfonyl chlorides and thiosulfonates from H2O 2-TiCl4
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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
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experimental part
p. 354 - 358
(2012/01/19)
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- Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system
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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
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supporting information; experimental part
p. 5095 - 5101
(2012/07/28)
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- TAPC-promoted synthesis of sulfonyl chlorides from sulfonic acids
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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
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experimental part
p. 2671 - 2674
(2011/12/04)
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- 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
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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
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experimental part
p. 3692 - 3695
(2012/01/11)
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- A novel, practical synthesis of sulfonyl chlorides from thiol and disulfide derivatives
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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
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experimental part
p. 2773 - 2776
(2010/02/28)
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- Direct conversion of thiols to sulfonyl chlorides and sulfonamides
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(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
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supporting information; experimental part
p. 9287 - 9291
(2010/03/04)
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- Inhibitors of Hepatitis C Virus
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Macrocyclic peptides are disclosed having the general formula: wherein R3, R3′, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 31
(2008/12/04)
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- MACROCYCLIC PEPTIDES AS HEPATITIS C VIRUS INHIBITORS
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Macrocyclic peptides having the general formula (I): are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 61-62
(2008/12/05)
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- Inhibitors of Hepatitis C Virus
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Macrocyclic peptides are disclosed having the general formula: wherein R3, R3′, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 30
(2008/12/04)
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- Inhibitors of Hepatitis C Virus
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Macrocyclic peptides are disclosed having the general formula: wherein R3, R′3, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
- -
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Page/Page column 31
(2008/12/04)
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- Hepatitis C Virus Inhibitors
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Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 29
(2008/12/05)
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- MACROCYCLIC PEPTIDES AS HEPATITIS C VIRUS INHIBITORS
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Macrocyclic peptides having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 59
(2008/12/05)
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- Hepatitis C virus inhibitors
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Macrocyclic peptides are disclosed having the general formula: wherein R′, R3, R3′, R4, R6, X, Q, and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
- -
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Page/Page column 34-35
(2010/11/26)
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- Hepatitis C virus inhibitors
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The present disclosure relates to tripeptide compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.
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Page/Page column 33-34
(2008/06/13)
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- Hepatitis C virus inhibitors
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Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 45
(2010/11/26)
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- Derivatives of N′-(1,5-diphenyl-1H-pyrazol-3-yl) sulfonamide with CB1 receptor affinity
-
The invention relates to compounds of formula (I): Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 are as defined herein. The invention also relates to the prepa
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Page/Page column 17-18
(2010/11/28)
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- PYRAZOLE DERIVATIVES FOR THE INHIBITION OF CDK' S AND GSK' S
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The invention provides compounds of the formula (I), or salts, tautomers, N-oxides or solvates thereof wherein: R1 is selected from: (a) 2,6-dichlorophenyl; (b) 2,6-difluorophenyl; (c) a 2,3,6-trisubstituted phenyl group wherein the substituents for the phenyl group are selected from fluorine, chlorine, methyl and methoxy; (d) a group R0; (e) a group R a; (f) a group Rlb; (g) a group Rlc; (h) a group Rld; and 0) 2,6-difluorophenylamino ; wherein R )0υ, r R> llaa, T Rj I1bD, T R) I1cC, r R> Iidα, r R?2zaa, r R>22bD and RJ are as defined in the claims. The compounds have activity as inhibitors of cdk kinase (such as cdkl or cdk2) and glycogen synthase kinase-3 activity.
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Page/Page column 159
(2008/06/13)
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- Hepatitis C virus inhibitors
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The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which inhibit the function of the NS3 protease (also referred to herein as “serine protease”) encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS3 protease.
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Page/Page column 31
(2008/06/13)
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- Sulfonyl chloride formation from thiol derivatives by N-chlorosuccinimide mediated oxidation
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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
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p. 4131 - 4134
(2008/03/13)
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- Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists
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The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.
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-
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- HEPATITIS C VIRUS INHIBITORS
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Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.
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- URICOSURIC AGENT
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A remedy for hyperuricemia which comprises a hydantoin derivative represented by general formula (I) or a salt thereof as the active ingredient, wherein Q represents cyclohexyl, cycloheptyl, cyclooctyl, 2,5-dimethylthien-3-yl, indan-2-yl or 2,5-dichlorophenyl. The uricosuric agent exerts a potent uricosuric effect on an animal experiment model while sustaining or gradually increasing the urine volume. Further, it has a low toxicity. Thus it is useful in the treatment of hyperuricemia or in the treatment and prevention of gout. It is expected that the effect of the uricosuric agent of sustaining or gradually increasing the urine volume would relieve the load on a patient of taking a large amount of water.
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- Cobalt(II)-Porphyrin Catalyzed Selective Functionalization of Alkanes with sulfurylchloride: A Remarkable Substituent Effect
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Cobalt(II)-porphyrin complex 1 and 2 catalyses the chlorination and sulfochlorination respectively of n-alkanes and cycloalkanes with sulfuryl chloride in benzene.The p-substituent of the benzene ring in the porphyrin complex 1 and 2 shows a remarkable chemoselectivity in these reactions.
- Khanna, Vibha,Tamilselvan, Pitchiah,Kalra, Swinder Jeet Singh,Iqbal, Javed
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p. 5935 - 5938
(2007/10/02)
-
- Synthesis of Alkanesulphonyl Chlorides from Alkylcobaloximes and Trichloromethanesulphonyl Chloride
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Alkyl- and substituted alkylcobaloximes react photochemically with trichloromethanesulphonyl chloride to give high yields of alkanesulphonyl chlorides. erythro-2-Phenylethylcobaloxime gives an equimolar mixture of erythro- and threo-2-phenylethanesulphonyl chloride and diastereoisomerically pure 1-phenylpropan-2-ylcobaloxime gives a 1:1 mixture of diastereoisomers of 1-phenylpropane-2-sulphonyl chloride.The reaction is believed to proceed through a non-chain process initiated by photolysis of the carbon-cobalt bond.The product alkanesulphonyl chloride is then formed, either by a direct attack of the alkyl radical on the sulphur of trichloromethanesulphonyl chloride, or through capture of the alkyl radical by sulphur dioxide and halogen abstraction by the so-formed alkanesulphonyl radical from trichloromethanesulphonyl chloride.The latter process seems the more likely.No evidence could be obtained for an intermolecular homolytic attack of trichloromethyl radicals on the saturated alkyl ligand.
- Bougeard, Peter,Johnson, Michael D.,Lampman, Gary M.
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p. 849 - 854
(2007/10/02)
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- Free-Radical Halogenations. 5. Reaction of Chlorosulfonyl Isocyanate with Alkanes
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The free-radical chain reactions of chlorosulfonyl isocyanate with alkanes can be initiated with either light or thermal initiators.The major products in these reactions are chlorides, with low yields of isocyanates and sulfonyl chlorides.On the basis of tertiary to primary hydrogen selectivity of about 120:1 and the relative reactivities of various substrates toward the abstracting radical from chlorosulfonyl isocyanate, the hydrogen-abstracting radical is suggested to be the NCO radical.
- Mosher, Melvyn W.
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p. 1875 - 1879
(2007/10/02)
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- Anthraquinone disperse dyestuffs
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1-Amino-4-hydroxy 2-p-alkoxy-benzenesulfonyloxy anthraquinone disperse dyestuffs have been prepared.
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