- 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
-
-
- 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)
-
- 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)
-
- Cell-Active Small Molecule Inhibitors of the DNA-Damage Repair Enzyme Poly(ADP-ribose) Glycohydrolase (PARG): Discovery and Optimization of Orally Bioavailable Quinazolinedione Sulfonamides
-
DNA damage repair enzymes are promising targets in the development of new therapeutic agents for a wide range of cancers and potentially other diseases. The enzyme poly(ADP-ribose) glycohydrolase (PARG) plays a pivotal role in the regulation of DNA repair mechanisms; however, the lack of potent drug-like inhibitors for use in cellular and in vivo models has limited the investigation of its potential as a novel therapeutic target. Using the crystal structure of human PARG in complex with the weakly active and cytotoxic anthraquinone 8a, novel quinazolinedione sulfonamides PARG inhibitors have been identified by means of structure-based virtual screening and library design. 1-Oxetan-3-ylmethyl derivatives 33d and 35d were selected for preliminary investigations in vivo. X-ray crystal structures help rationalize the observed structure-activity relationships of these novel inhibitors.
- Waszkowycz, Bohdan,Smith, Kate M.,McGonagle, Alison E.,Jordan, Allan M.,Acton, Ben,Fairweather, Emma E.,Griffiths, Louise A.,Hamilton, Niall M.,Hamilton, Nicola S.,Hitchin, James R.,Hutton, Colin P.,James, Dominic I.,Jones, Clifford D.,Jones, Stuart,Mould, Daniel P.,Small, Helen F.,Stowell, Alexandra I. J.,Tucker, Julie A.,Waddell, Ian D.,Ogilvie, Donald J.
-
p. 10767 - 10792
(2019/01/04)
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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
-
supporting information
p. 2286 - 2295
(2017/07/24)
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- Method for synthetizing 2-naphthalene sulfonyl chloride by phosphorus oxychloride
-
The invention discloses a method for synthetizing 2-naphthalene sulfonyl chloride by phosphorus oxychloride. The method comprises the following steps: 1) successively adding 2-naphthalene sulfonic acid sodium salt and phosphorus oxychloride into a solvent to obtain reaction liquid a; 2) causing the reaction liquid a obtained in the step 1) to react for 4-12h at the temperature of 50-110DEG C to obtain mixed liquor b; 3) after the mixed liquor b obtained in the step 2) is continuously evaporated, successively cleaning, filtering, and carrying out reduced pressure distillation to obtain the 2-naphthalene sulfonyl chloride. The method has the advantages of simplicity in operation, small use amount of solvent, low cost, high product yield, high purity and convenience in solvent recovery, and environment pollution is greatly lightened.
- -
-
Paragraph 0067; 0068; 0069; 0070; 0071; 0072
(2016/10/31)
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- Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides
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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
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p. 3051 - 3057
(2016/04/26)
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- Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water
-
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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p. 3125 - 3131
(2014/06/10)
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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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- Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids
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A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.
- Debergh, J. Robb,Niljianskul, Nootaree,Buchwald, Stephen L.
-
supporting information
p. 10638 - 10641
(2013/08/23)
-
- 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
-
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 synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T
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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
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p. 2147 - 2151
(2013/12/04)
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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)
-
- 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
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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)
-
- 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
-
supporting information; experimental part
p. 5095 - 5101
(2012/07/28)
-
- 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
-
experimental part
p. 2671 - 2674
(2011/12/04)
-
- 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)
-
- 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
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experimental part
p. 2315 - 2320
(2011/10/13)
-
- Substituted Disulfonamide Compounds
-
Substituted disulfonamide compounds corresponding to formula I: In which R1, R2, R3, R4a, R4b, R5a, R5b, R8, R9a, R9b, R10, R11, a, b, s, t and A have defined meanings, pharmaceutical compositions containing one or more such compounds, processes for preparing such compounds, and a method of using such compounds for the treatment or inhibition of pain and/or other conditions mediated by the bradykinin receptor 1 (BR1).
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Page/Page column 37
(2010/06/22)
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- A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides
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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
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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
-
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)
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- An easy microwave-assisted synthesis of sulfonamides directly from sulfonic acids
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(Chemical Equation Presented) An easy and handy synthesis of sulfonamides directly from sulfonic acids or its sodium salts is reported. The reaction is performed under microwave irradiation, has shown a good functional group tolerance, and is high yielding.
- De Luca, Lidia,Giacomelli, Giampaolo
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p. 3967 - 3969
(2008/09/19)
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- Novel naphthalene-N-sulfonyl-D-glutamic acid derivatives as inhibitors of MurD, a key peptidoglycan biosynthesis enzyme
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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
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scheme or table
p. 7486 - 7494
(2009/11/30)
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- A new, mild preparation of sulfonyl chlorides
-
A new method was developed for the preparation of sulfonyl chlorides from sulfonic acids under neutral conditions using 2,4,6-trichloro-1,3,5-triazine as chlorinating agent.
- Blotny, Grzegorz
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p. 1499 - 1501
(2007/10/03)
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- New compounds
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The present invention relates to substituted bis-arylsulfonamide and arylsulfonamide compounds of the general formula (I) or the formula (II), which compounds are potentially useful for the prophylaxis and treatment of medical conditions relating to obesity, type II diabetes and/or disorders of the central nervous system.
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- Bispiperidines as antithrombotic agents
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Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents
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- METALLOPROTEASE INHIBITORS
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Compound of formula (I): STR1 in which: m, n, which are identical or different, represent 0, 1 or 2,R 1, R. sub.2, which are identical or different, represent hydrogen, optionally substituted alkyl, aryl, or form with the carbon atom carrying them carbonyl or (C 3-C 7)cycloalkyl,R 3 represents hydrogen, alkyl, hydroxyl or aryl,R 4 represents any of the groups as defined in the description,X represents--SO 2--,--CO--or--SO 2 NH--,R 5 represents optionally substituted alkyl, (C 3-C 7) cycloalkyl, aryl or heterocyclic,A represents an aryl ring or a heterocycle,its isomers as well as its addition salts with a pharmaceutically acceptable acid or base and medicinal products containing the same are useful as metalloprotease inhibitors.
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- Preparation of sulfonamides from sodium sulfonates: Ph3P·Br2 and Ph3P·Cl2 as a mild halogenating reagent for sulfonyl bromides and sulfonyl chlorides
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Arene- and alkanesulfonamides were prepared by treatment of the corresponding sodium sulfonates with triphenylphosphine dibromide or dichloride followed by amines in the presence of triethylamine via sulfonyl halides. Reactions of sodium aminosulfonates gave cyclized products. Amidation of p-toluenesulfonic acid with triphenylphosphine dichloride was also examined to give N-benzyl-p-toluenesulfonamide. Methyl p- toluenesulfonate was obtained by esterification of sodium p-toluenesulfonate via p-toluenesulfonyl chloride.
- Kataoka, Tadashi,Iwama, Tetsuo,Setta, Tomofumi,Takagi, Atsuko
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p. 423 - 426
(2007/10/03)
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- Preparation of 2-chloro-5-methyl-pyridine
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A process for the preparation of 2-chloro-5-methylpyridine of the formula STR1 which comprises reacting 3-methyl-pyridine-1-oxide of the formula STR2 with a chlorinating agent of the formula STR3 in which R1 represents alkyl, halogenoalkyl, cycloalkyl, optionally substituted aryl, NR2 R3 or OR4 in which R2 and R3 individually represent alkyl, cycloalkyl or aryl or together represent alkanediyl or oxaalkanediyl and R4 represents alkyl, cycloalkyl or optionally substituted aryl, in the presence of a basic organic nitrogen compound and in the presence of a diluent at a temperature between about -20° C. and +150° C.
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- The Electrostatically Paired Bis(dimethyl sulfoxide)(tetrakis(1-methylpyridinium-4-yl)porphinato)iron(III)/(4,4',4'',4'''-Tetrasulfonatophthalocyaninato)zinc(II) System. Solution Structure and Dynamics
-
The electrostatic pairing interactions between the bis(dimethyl sulfoxide)(tetrakis(1-methylpyridinium-4-yl)porphinato)iron(III) cation, 5+, and the (4,4',4'',4'''-tetrasulfonatophthalocyaninato)zinc(II) anion, 4-, have been studied in dimethyl sulfoxide (DMSO) solution.Measurements of the electrostatic pair association constant, Kep, and its dependence upon ionic strength (Me4NClO4) were made with standard visible spectroscopic techniques while association dynamics were studied by NMR methods in DMSO-d6 solution.The exchange rate lawfor electrostatic pair formation takes into account DMSO solvent exchange of the iron porphyrin-solvent complex, and the exchange lifetime for the pair at ionic strength of 1 mM is calculated to be ca. 0.24 s at 25 deg C.Solution structural assessments were made by using measurements of the intermolecular dipolar relaxation of the (tetrasulfonatophthalocyaninato)zinc(II) protons due to the paramagnetic high-spin iron(III) center in the electrostatic pair.The structural model developed permitted calculation of a set of possible iron positions with respect to the phthalocyanine plane which are consistent with a cofacial dimeric structure displaying ?-? interactions due to pyrrole ring overlap.
- Goodwin, John A.,Scheidt, W. Robert
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p. 4432 - 4439
(2007/10/02)
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- An Improved Synthesis of Arylsulfonyl Chlorides from Aryl Halides
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Arylsulfonyl chlorides 8 are prepared from aryl bromides 5 via lithium arylsulfinates 7 in excellent yields.
- Hamada, Tatsuo,Yonemitsu, Osamu
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p. 852 - 854
(2007/10/02)
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- Process for preparing amides by reaction in presence of molecular sieve
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There is provided a process for preparing amides which comprises reacting an amine, or an amide, and an acid halide, or anhydride, in suitable molecular proportions, in an inert organic diluent, in the presence of an effective amount of a molecular sieve, until the reaction is completed, separating the molecular sieve, and recovering the amide from the organic mother liquor.
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- Method of producing quaternary pyridinium compounds
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The method of preparing quaternary pyridinium compounds having the formula STR1 WHEREIN R represents alkyl, STR2 in which A is phenyl, naphthyl, carbostyrilyl, pyrazolinyl and substituted derivatives thereof where the substitutents are selected from the group consisting of alkyl having 1 to 4 carbon atoms, NO2, Cl, Br, phenyl, nitrophenyl and methylsulfonate; B is -O-alkylene-, STR3 AND C is selected from the group consisting of hydrogen, NHCOR1 and, when B is -O-alkylene, C can also be --OR2 -- where R1 is alkyl of 1 to 4 carbon atoms and R2 is alkylene of 1 to 4 carbon atoms; and wherein R4 represents lower alkyl having 1 to 6 carbon atoms, halophenyl, alkylphenyl or naphthyl, m represents an integer of 1 or 2 and m' is equal to m. The process for preparing the particularly designated compounds above comprises contacting pyridine and a hydroxy-containing compound having the formula: R'--(OH)n wherein R' represents alkyl, STR4 in which A' is phenyl, naphthyl, carbostyrilyl, pyrazolinyl and substituted derivatives thereof where the substituents are selected from the group consisting of alkyl having 1 to 4 carbon atoms, NO2, Cl, Br, phenyl, nitrophenyl and hydroxy; B, C, R1 and R2 are as defined above; and n is an integer of 1 or 2 and is equivalent to m defined above; reacting the pyridine and said hydroxy-containing compound in the presence of a sulfonyl halide having the formula R4 SO2 X wherein R4 is as defined above and X is Cl, Br or F; and conducting the reaction at an elevated temperature up to the reflux temperature of the reaction mixture. The quaternary pyridinium compounds can be used to prepare cationic surfactants, cationic pharmaceuticals, cationic dyestuffs, pesticides, fungicides and agricultural chemicals.
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