- Copper-catalyzed synthesis of sulfonamides from nitroarenes: Via the insertion of sulfur dioxide
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Nitroarenes are used as the coupling partners in the preparation of sulfonamides via the insertion of sulfur dioxide. A three-component reaction of arylboronic acids, nitroarenes, and potassium metabisulfite under copper catalysis proceeds smoothly, giving rise to a range of sulfonamides in good to excellent yields with broad substrate scope. Various functional groups including hydroxyl, cyano, amino, and carbonyl are all tolerated. A plausible mechanism is proposed, showing that arylsulfinate is the intermediate and the copper-assisted interaction of the nitroarene and arylsulfinate is the key step. This approach is also extended to the late-stage modification of a currently marketed drug (flutamide).
- Wang, Xuefeng,Yang, Min,Kuang, Yunyan,Liu, Jin-Biao,Fan, Xiaona,Wu, Jie
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p. 3437 - 3440
(2020/03/30)
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- Metal-free one-pot synthesis of N-arylsulfonamides from nitroarenes and sodium sulfinates in an aqueous medium
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A metal-free one-pot two-step synthesis of sulfonamides from readily available nitroarenes and sodium arylsulfinates in a mixture of methanol and water has been developed. In this procedure, the aryl amines were produced in situ by the reduction of nitroarenes mediated by diboronic acid, and then coupled with sodium arylsulfinates in the presence of iodine. A series of N-arylsulfonamides with various functional groups were obtained in moderate to good yields under the optimal reaction conditions. In addition, this one-pot process is applicable for gram-scale synthesis.
- Jiang, Xiaolan,Zhang, Kaili,Zhao, Rongrong,Bai, Die,Wang, Jinlong,Li, Binbin,Liu, Qixing,Zhou, Haifeng
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supporting information
(2020/09/10)
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- Preparation method of sulfamide compound
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The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of a sulfamide compound, wherein the structure of the sulfamide compound synthesizedby the method is characterized and confirmed by H NMR and C NMR. The method comprises the following steps: in an organic solvent, carrying out a reaction on an aryl diazonium salt, a sulfur dioxide solid complex and an aryl nitroso compound in the presence of a reducing agent under a heating condition, wherein the diazonium salt and the sulfur dioxide solid complex act to generate aryl sulfonyl free radicals, and then the aryl nitroso compound is attacked; and reducing the generated hydroxylamine to obtain the sulfamide compound. The preparation method of the compound has the advantages of mild conditions, simplicity, high efficiency, no need of catalysts, no need of pre-synthesis of sulfonyl chloride or sodium sulfonate reagents, wide substrate application range, strong functionalgroup compatibility, convenience in separation and purification, and excellent industrial and medicinal chemical application values.
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Paragraph 0026-0029
(2020/06/02)
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- Sequential C-S and S-N Coupling Approach to Sulfonamides
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A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.
- Chen, Kai,Chen, Wei,Han, Bing,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
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supporting information
p. 1841 - 1845
(2020/03/04)
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- Synthesis of N-phenylsulfonamide derivatives and investigation of some esterase enzymes inhibiting properties
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In this study, synthesis of nine N-phenylsulfonamide derivatives was designed by starting from aniline, which is the simplest aromatic amine. These compounds were obtained in yields between 69 and 95%. Inhibitory properties of synthesized compounds on car
- Akin Kazancioglu, Elif,Senturk, Murat
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- Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound
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The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.
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Paragraph 0152-0156
(2019/11/12)
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- Multicomponent synthesis of sulfonamides from triarylbismuthines, nitro compounds and sodium metabisulfite in deep eutectic solvents
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A sustainable synthesis of sulfonamides using a copper-catalysed process starting from triarylbismuthines, Na2S2O5 and nitro compounds in a Deep Eutectic Solvent (DES) as a reaction medium is described. Thus, triarylbismuthines are used as reagents for the incorporation of SO2 into organic motifs. The bismuth salts formed as by-products can be easily removed from the crude reaction mixture by precipitation with water, while the use of volatile organic compounds (VOCs) as solvents can be avoided in the entire process. The eutectic mixture employed as the solvent is fully characterised, with the preliminary results proving its low toxicity. The designed DES also allows for a novel multicomponent reaction which saves time and reduces purification steps, energy and cost.
- Marset, Xavier,Torregrosa-Crespo, Javier,Martínez-Espinosa, Rosa M.,Guillena, Gabriela,Ramón, Diego J.
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supporting information
p. 4127 - 4132
(2019/08/07)
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- Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines
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A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by arylhydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance (up to 36 examples). The protocol was proposed to take place through the free radical pathway based on the results of control reactions and EPR analysis.
- Dong, Wanrong,Liu, Chaoyang,Ma, Xinchi,Zhang, Yingjun,Peng, Zhihong,Xie, Dexun,An, Delie
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p. 3886 - 3893
(2019/06/18)
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- Sulfonyl imide or sulfonamide of the denitrification arylation method and product and application
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A sulfonyl imide or sulfonamide of the denitrification arylation method and product and application, sulfonimide or sulfonamide of the denitrification arylation method, comprises the following steps: to arylhydrazine and sulfonyl imide or sulfonamide as raw material, the catalyst palladium salt, alkali, solvent and oxidizing agent in the presence of, prepared N - aryl sulfonyl imide or N - aryl sulfonamides. The sulfonimide or sulfonamide of the denitrification arylation method, by adopting the arylhydrazine and sulfonimide or sulfonamide as raw materials used to prepare N - aryl sulfonyl imide or N - aryl sulfonamides, arylhydrazine because of having low cost, high reactivity and easy accessibility and the like, can make the sulfonyl imide or a sulfonamide for the arylation of the method cost is relatively low. The arylhydrazine as aryl group donor, the reaction by-product is N2 And H2 O, so it has the characteristics of green and environmental protection.
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Paragraph 0066-0073
(2019/03/31)
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- Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates
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An unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the N–C bond in isocyanates, reacted with aryne precursor
- Seo, Jeong Hoon,Ko, Haye Min
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supporting information
p. 671 - 674
(2018/01/19)
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- Synthesis of N-arylsulfonamides through a Pd-catalyzed reduction coupling reaction of nitroarenes with sodium arylsulfinates
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A novel one-step direct reductive coupling reaction between nitroarenes and sodium arylsulfinates was realized in the presence of an inexpensive Pd/C catalyst. In this procedure, readily available nitroarenes are employed as the nitrogen sources, and sodium arylsulfinates serve as both coupling partners and reductants. The method features high efficiency by using cheap Pd/C with low catalyst loading and good functional group tolerance in the absence of any additional reductants or ligands. This facile and mild synthetic method enables the high efficiency synthesis of functionalized N-arylsulfonamides from readily available substrates.
- Yang, Bo,Lian, Chang,Yue, Guanglu,Liu, Danyang,Wei, Liyan,Ding, Yi,Zheng, Xiancai,Lu, Kui,Qiu, Di,Zhao, Xia
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supporting information
p. 8150 - 8154
(2018/11/23)
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- Method for ultrasound-assisted synthesis of N-arylsulfonamide
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The invention discloses a method for ultrasound-assisted synthesis of N-arylsulfonamide. N-arylsulfonamide compound is synthesized by series reaction of nitro reduction/sulfonyl chloride reduction/sulfonamidation with taking aromatic nitro compounds, sulfonyl chloride and iron powder as raw materials under ultrasonic stirring conditions. Water is used as a reaction medium and a hydrogen source inthe reaction. The method has the advantages of cheap and easily obtained raw materials, simple and mild reaction conditions, environmental friendliness, saving energy, high reaction selectivity and high yield, excellent compatibility of substrate functional groups and high application value.
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Paragraph 0101; 0102; 0103
(2018/11/27)
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- Synthesis of: N -arylsulfonamides via Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium
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A fascinating Fe-promoted protocol for the synthesis of N-arylsulfonamides has been developed. Starting from commercially available nitroarenes and sulfonyl chlorides, moderate to excellent yields of the corresponding N-arylsulfonamides can be obtained. In particular, Fe dust serves as the sole reductant in the transformation and it can be easily performed on a large scale.
- Jiang, Jun,Zeng, Sheng,Chen, De,Cheng, Chaozhihui,Deng, Wei,Xiang, Jiannan
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supporting information
p. 5016 - 5020
(2018/07/25)
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- Palladium-catalyzed desulfitative arylation of sulfonamides with sodium arylsulfinates
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A Pd(II)-catalyzed desulfitative arylation protocol between sulfonamides and sodium arylsulfinates was herein reported. The direct arylation reaction was successfully achieved by a Pd(II)/Ag(I)-mediated system without participation of any external ligands with a release of SO2. And different N-aryl sulfonamides were obtained readily in up to 86% yields, exhibiting good functional groups tolerance (25 examples).
- Zhao, Zijian,Lian, Yan,Zhao, Chang,Wang, Bing
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supporting information
p. 1436 - 1442
(2018/06/01)
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- Iron-catalyzed N -arylsulfonamide formation through directly using nitroarenes as nitrogen sources
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One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.
- Zhang, Weixi,Xie, Junyao,Rao, Bin,Luo, Meiming
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p. 3504 - 3511
(2015/04/14)
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- Palladium-catalyzed arylation of aryl sulfonamides with cyclohexanones
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Pd-catalyzed intermolecular aerobic dehydrogenative aromatizations have been developed for the arylation of aryl sulfonamides with cyclohexanones. Various N-aryl sulfonamides were selectively obtained in good yields using molecular oxygen as oxidant. The reaction tolerated a wide range of functionalities.
- Cao, Xiangxiang,Bai, Yang,Xie, Yanjun,Deng, Guo-Jun
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- BICYCLOSULFONYL ACID (BCSA) COMPOUNDS AND THEIR USE AS THERAPEUTIC AGENTS
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This invention pertains generally to the field of therapeutic compounds, and more particularly, to certain bicyclosulfonyl acid (BCSA) compounds which act as inhibitors of Tumour Necrosis Factor-α Converting Enzyme (TACE). The compounds are useful in the
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Page/Page column 74-75; 143-144
(2009/01/20)
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- Synthesis of biotinylated photoaffinity probes based on arylsulfonamide γ-secretase inhibitors
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Synthesis and biological evaluation of an arylsulfonamide class of γ-secretase inhibitors are described. Design, synthesis, and biological evaluation of multifunctional molecular probes harboring a benzophenone photophore as a cross-linking group and a biotin tag are also reported.
- Fuwa, Haruhiko,Hiromoto, Kenichi,Takahashi, Yasuko,Yokoshima, Satoshi,Kan, Toshiyuki,Fukuyama, Tohru,Iwatsubo, Takeshi,Tomita, Taisuke,Natsugari, Hideaki
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p. 4184 - 4189
(2007/10/03)
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