- 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 Sultams and Cyclic N-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C-H Amidation
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Cyclic sulfonamides (sultams) play a unique role in drug discovery and synthetic chemistry. A direct synthesis of sultams by an intramolecular C(sp3)-H amidation reaction using an iron complex in situ derived from Fe(ClO4)2 and aminopyridine ligand is reported. This strategy features a readily available catalyst and tolerates a broad variety of substrates as demonstrated by 22 examples (up to 89% yield). A one-pot iron-catalyzed amidation/oxidation procedure for the synthesis of cyclic N-sulfonyl ketimines is also realized with up to 92% yield (eight examples). The synthetic utility of the method is validated by a gram-scale reaction and derivatization of the products to ring-fused sultams.
- Zhong, Dayou,Wu, Di,Zhang, Yan,Lu, Zhiwu,Usman, Muhammad,Liu, Wei,Lu, Xiuqiang,Liu, Wen-Bo
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supporting information
p. 5808 - 5812
(2019/08/26)
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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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- Tert -Butyl Hypochlorite Mediated Oxidative Chlorination of S -Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides
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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
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p. 3186 - 3190
(2015/10/19)
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- Clean and economic synthesis of alkanesulfonyl chlorides from S-alkyl isothiourea salts via bleach oxidative chlorosulfonation
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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
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p. 225 - 229
(2014/03/21)
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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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- 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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- 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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- A new synthesis of alkane and polyfluoroalkanesulfonyl chlorides
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This study describes a new and advantageous procedure for the synthesis of alkanesulfonyl chlorides (2) by the reaction of alkyl thiocyanates (1) with sulfuryl chloride in a mixture of acetic acid and water. The alkanesulfonyl chlorides were obtained in good yields.
- Benfodda, Zohra,Guillen, Franck,Arnion, Helene,Dahmani, Abdelkader,Blancou, Hubert
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experimental part
p. 355 - 361
(2010/07/16)
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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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- Pharmaceutical Compositions Based on Fluorinated Sulphamides and Sulphinimides
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Pharmacuetical composition comprising compounds of formula (I): [in-line-formulae]NZ1Z2Z3 ??(I) [/in-line-formulae] in which: Z1, Z2, Z3 each independently of the others represents: a hydrogen atom; C1-C6-alkyl group; a group —SO2R3 wherein R3 represents a linear or branched C1-C12-alkyl, -alkenyl or -alkynyl group, a C3-C10-cycloalkyl group or a C6-C10-aryl group, a (C1-C6)-alkyl-(C6-C14)-aryl group, or a C5-C10-heteroaryl group; it being understood that at least one of the groups Z1, Z2, Z3 represents a group of formula (II) [in-line-formulae]X—RF—(CH2)n—SO2—??(II) [/in-line-formulae] X, RF and n being as defined in claim 1.
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Page/Page column 9
(2008/06/13)
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- Method for making alkanesulphonyl chlorides
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In the process according to the invention for the manufacture of an alkanesulphonyl chloride RCH2—SO2Cl by oxidative chlorolysis of the corresponding mercaptan RCH2—SH, the mercaptan and water are introduced into the reaction mixture in the form of a dispersion of water in the mercaptan. This makes it possible to obtain both an alkanesulphonyl chloride of very good quality and a hydrochloric acid of commercial grade.
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- N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing
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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
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p. 5145 - 5149
(2007/10/03)
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- ALPHA-AMINO SULFONYL HYDROXAMIC ACIDS AS MATRIX METALLOPROTEINASE INHIBITORS
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A compound of formula I or pharmaceutical acceptable salts thereof, STR1 wherein R 1 is isopropyl, 2-methylbut-2yl, phenyl, benzyl, or 1H-indol-3ylmethyl; R 2 is n-octyl, phenyl, or phenyl substituted with methoxy, fluoro, or bromo, are matrix metalloproteinase inhibitors.
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- Solid-state organic reactions proceeding by pulverization: Oxidation and halogenation with iodosobenzene and inorganic solid-supports
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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
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p. 13737 - 13750
(2007/10/03)
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- Novel One-Step Synthesis of Sulfonyl Chlorides from Sulfides with Iodosobenzene and Hydrogen Chloride-Treated Silica Gel
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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
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p. 891 - 892
(2007/10/02)
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- Oxidation of thiols, disulfides and thiolsulfonates
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Alkanesulfonic acids and alkanesulfonyl chlorides, free of undesirable side products arising from side-chain chlorination, are prepared by oxidation with hydrogen peroxide of the corresponding alkanethiol, dialkyldisulfide or alkyl alkanethiolsulfonate mixed with aqueous hydrochloric acid.
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- Novel sulfonamide derivatives
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A compound, or pharmaceutically acceptable salt thereof, having the formula: STR1 wherein X is STR2 wherein R is C3 -C12 alkyl or aralkyl, branched or unbranched, unsubstituted aryl, haloaryl, or C3 -C22 alkenyl, branched or unbranched; wherein R1 is H, OH or OCH3, and wherein R2 is OH or H, at least one of R1 and R2 being OH or OCH3. These sulfonamides have analgesic and anti-irritant activity when administered to humans and lower animals.
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- N-sulfonyl-N-dihalophenylimidazolidinediones
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3-(3' -Dihalophenyl)-1-sulfonylimidazolidine-2,4-5'-diones of the formula: STR1 wherein X is a halogen atom, R1 is a C1 -C12 alkyl group, a C2 -C4 alkenyl group or a halogenated C1 -C4 alkyl group having 1 to 3 halogen atoms, and R2 and R3 are individually a hydrogen atom or a methyl group, which show high microbicidal activities against various fungi and bacteria without any material toxicity to mammals and which plants and can be produced by reacting the corresponding 1-unsubstituted compound with a sulfonyl halide.
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