- Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
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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
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- 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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- 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.
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supporting information
p. 10638 - 10641
(2013/08/23)
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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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- 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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- Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide
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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)
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- Synthesis, pharmacological activity and comparative QSAR modeling of 1,5-N,N′-substituted-2-(substituted naphthalenesulphonyl) glutamamides as possible anticancer agents
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Based on our earlier QSAR study, a series of 1, 5-N,N′-substituted-2-(substituted naphthalenesulphonyl) glutamamides were synthesized as possible anticancer agents. Anticancer activities of these synthesized compounds were evaluated in vivo on Swiss Albino mice against Ehrlich Ascites Carcinoma (EAC) cells where inhibitions of tumor cell and tumor weight were considered as biological activity parameters. A comparative QSAR study was done with a set of descriptors and logarithm of tumor cell inhibition. The result shows the importance of topological parameters like ETSA and RTSA indices as well as electronic parameter like Wang-Ford charges of different atoms. Electrophilic attack at atom number 5 and increased number of chlorine atom may be favorable whereas presence of methoxy group at the atom number 8 in naphthalene ring may be detrimental to the activity.
- Halder, Amit Kumar,Adhikary, Nilanjan,Maity, Milan Kumar,Jha, Tarun
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scheme or table
p. 1760 - 1771
(2010/06/21)
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- Substituted Disulfonamide Compounds
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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 38
(2010/06/22)
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- A new method for the synthesis of dinaphtho[1,2-b;2′,1′-d] thiophenes and selenophenes
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Naphthalene-1-sulfonic acid dimethylamides were treated with n-BuLi and elemental sulfur or selenium to afford dinaphtho[1,2-b:2′,1′-d] thiophenes and selenophenes, respectively. This is the first example of making two C-S/Se bonds and a C-C bond in a single step at room temperature and also demonstrates a useful method for the synthesis of both thiophenes and selenophenes on naphthalene. In the case of the reactions of elemental selenium, diselenides were also obtained along with dinaphtho[1,2-b:2′,1′-d] selenophenes. The structure of dinaphtho[1,2-b:2′,1′-d]thiophene was characterized by X-ray crystallography as a representative molecule.
- Alam, Ashraful,Ohta, Hidetoshi,Yamamoto, Tatsuya,Ogawa, Satoshi,Sato, Ryu
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p. 239 - 248
(2008/02/08)
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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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- 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
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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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- Process for the preparation of naphthalenesulphonyl chloride
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In a process for the preparation of a naphthalenesulphonyl chloride by reacting an alkali metal salt or ammonium salt of a naphthalenesulphonic acid with thionyl chloride in the presence of a catalytically active substance the improvement wherein the reaction is carried out in the presence of an optionally substituted pyridine, tertiary aliphatic amine, secondary amidine and/or quaternary ammonium salt.
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- CONFORMATIONAL ANALYSIS AND PHOTOCHeMICAL BEHAVIOUR OF SULFOXIDES IN THE NAPHTHOTHIOPYRAN AND NAPHTHOTHIOPYRAN SERIES
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The sulfoxides derived from 2,3-dihydro-4H-naphthothiopyran and its 4-phenyl and 4-oxo derivatives, as well as the analogous sulfoxides in the 2,3-dihydro-1H-naphthothiopyran series, have been synthesized and their structures established by spectroscopic methods, especially 1H and 13C nmr.On the photolysis these sulfoxides have been found to react by a rather inefficient photochemical deoxygenation pathway.
- Still, Ian W. J.,Arora, Parkash C.,Hasan, S. Khaquan,Kutney, Gerald W.,Lo, LAwrence Y. T.,Turnbull, Kenneth
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p. 199 - 209
(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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