- KCC-1 aminopropyl-functionalized supported on iron oxide magnetic nanoparticles as a novel magnetic nanocatalyst for the green and efficient synthesis of sulfonamide derivatives
-
A new magnetic nanocatalyst (Fe3O4@KCC-1-npr-NH2) was synthesized directly through the reaction of Fe3O4@KCC-1 with (3-aminopropyl) triethoxysilane (APTES) using a hydrothermal protocol. Prepared nanocomposite was used as a magnetically reusable nanocatalyst for an efficient synthesis of a broad range of sulfonamide derivatives in water as a green solvent at room temperature and the products are collected by filtration with excellent yields (85–97%). The nanocatalyst could be remarkably recovered and reused after ten times without any significant decrease in activity. This mild and simple synthesis method offers some advantages including short reaction time, high yield and simple work-up procedure.
- Azizi, Sajjad,Shadjou, Nasrin,Hasanzadeh, Mohammad
-
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- Copper iodide nanoparticles-decorated porous polysulfonamide gel: As effective catalyst for decarboxylative synthesis of N-Arylsulfonamides
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A porous cross-linked poly (ethyleneamine)-polysulfonamide (PEA-PSA) as a novel organic support system is synthesized in the presence of silica template by nanocasting technique. The paper demonstrates immobilization of CuI nanoparticles inside the pores (PEA-PSA?CuI) for the facile recovery and recycling of these nanoparticles. The presence of porous PEA-PSA and PEA-PSA?CuI nanocomposites was confirmed using FT-IR spectroscopy, FE-SEM, EDX, TGA, XRD, TEM, BET, XPS, WDX, 1H NMR, and ICP-OES techniques. The PEA-PSA?CuI along with Ag(I)/K2S2O8 was implemented as a reusable cooperative catalyst-oxidant system in the N-arylation of p-toluenesulfonamide with substituted carboxylic acids in mild condition. So, the novel decarboxylative cross-coupling catalyzed by copper and silver has been developed. Aromatic, secondary and tertiary aliphatic acids underwent high efficient decarboxylative processes with p-toluenesulfonamide to afford the corresponding products. This method provides a practical approach for the flexible synthesis of sulfonamides from the readily affordable substrates. The catalyst is highly reusable and efficient, especially in terms of time and yield of the desired product.
- Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin,Rakhtshah, Jamshid,Yousefi Seyf, Jaber,Ali Arabian, Iman
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-
- Copper-mediated regioselective efficient direct ortho-nitration of anilide derivatives
-
The mild and readily available Cu(NO3)2 mediated ortho nitration of anilides with broad substrate using K2S2O8 as an oxidant in the absence of any other metal catalyst and nitrating agent under mild conditions was reported for the first time.
- Reddy Depa, Manmohan,Potla, Suneetha,Narkhede, Umesh C.,Jadhav, Vinod D.,Vidavalur, Siddaiah
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supporting information
(2020/07/20)
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- Synthesis of SMZ derivatives and investigation of effects on germination, root, and plant growth of Arabidopsis thaliana L.
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A series of sulfonamide derivatives were synthesized by reactions with various functional groups containing benzenesulfonyl chlorides and aniline derivatives under different substitution reaction conditions. The structures of SMZ derivatives were confirmed with melting point, FT-IR, 1 H NMR, 13 C NMR, and LC-MS/MS techniques. In order to investigate the cytotoxic effects of these derivatives, we used a model plant species. The synthesized compounds (S1–S5) and sulfamethazine (SMZ) as a positive control were applied to Arabidopsis thaliana seeds. Our results indicated that S3 and S4 induced shorter roots and lower wet weight in plants. Plants treated with S2 and S5 showed no growth effects, similar to the untreated control group, while S1 slightly reduced root length and wet weight. These results suggest that S3 and the newly synthesized S4 derivatives have potential for use as herbicides since they possess cytotoxic effects on A. thaliana plants.
- Güng?r, Tu?ba,C?mert ?nder, Ferah,Sezer, Fatih,?zbilen, Asl?han,Ta?kin, Kemal Melih,Ay, Mehmet
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p. 1123 - 1133
(2019/09/10)
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- A microwave-assisted approach to N-(2-nitrophenyl)benzenesulfonamides that enhanced peroxidase activity in response to excess cadmium
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A facile and efficient approach to N-(2-nitrophenyl) benzenesulfonamides was developed under microwave irradiation. A series of pyrabactin analogues containing nitrophenyl scaffold was obtained in excellent yields. In addition, the method was pretty suitable to prepare flusulfamide. Significantly, the 3ae could enhance POD activity in response to heavy metal stress.
- Huang, Zhi-You,Liu, Min,Mao, Yi-Jun,Chen, Yu-De,Wang, Yan-Ping,Liu, Chong
-
supporting information
p. 626 - 629
(2019/02/01)
-
- 3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature
-
Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.
- Chaudhary, Renu,Natarajan, Palani,Rani, Neetu,Sakshi,Venugopalan, Paloth
-
supporting information
(2019/12/30)
-
- Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation
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In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).
- Polley, Arghya,Bairy, Gurupada,Das, Pritha,Jana, Ranjan
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supporting information
p. 4161 - 4167
(2018/09/21)
-
- Visible-Light-Mediated Nitration of Protected Anilines
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The photocatalytic nitration of protected anilines proceeds with riboflavin tetraacetate as an organic photoredox catalyst. Sodium nitrite serves as the NO2 source in this visible-light-driven room temperature reaction. Various nitroanilines are obtained in moderate to good yields without the addition of acid or stoichiometric oxidation agents. The catalytic cycle is closed by aerial oxygen as the terminal oxidant.
- Düsel, Simon J. S.,K?nig, Burkhard
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p. 2802 - 2807
(2018/03/09)
-
- Efficient copper-catalyzed N-arylation of NH-containing heterocycles and sulfonamides with arenediazonium tetrafluoroborates
-
A practical copper-catalyzed N-arylation of NH-containing heterocycles with arenediazonium tetrafluoroborates has been developed using CuCl as catalyst and K2CO3 as additive under ligand-free conditions. This reaction system has wide substrate scope including imides, 1H-pyrazole, 1H-tetrazoles, 1,2-benzisothiazol-3(2H)-one, and related sulfonamides and gives moderate to excellent yields (up to 95%) of the desired products. This strategy is very general, simple, environmentally friendly, and tolerant of oxygen.
- Ouyang, Yu-Qing,Yang, Zhen-Hua,Chen, Zhong-Hui,Zhao, Sheng-Yin
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p. 771 - 778
(2017/04/06)
-
- Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from N-Ts-Anilines and Styrenes
-
A Pd-catalyzed intermolecular oxidative annulation between N-Ts-anilines and styrenes was developed. This method offers a straightforward and robust approach to a wide range of 3-arylindoles using readily available starting materials with good functional-group tolerance and high regioselectivity and efficiency. Further elaboration of the products obtained from this process provided access to highly functionalized and structurally diverse indoles, for example, 3-(indol-3-yl)carbazoles, 1,9-dihydropyrrolo-[2,3-b]carbazoles, and 3′-aryl-3,5′-biindoles.
- Youn, So Won,Ko, Tae Yun,Jang, Young Ho
-
supporting information
p. 6636 - 6640
(2017/05/29)
-
- Design and synthesis of sulfonamide-substituted diphenylpyrimidines (SFA-DPPYs) as potent Bruton's tyrosine kinase (BTK) inhibitors with improved activity toward B-cell lymphoblastic leukemia
-
A new series of diphenylpyrimidine derivatives (SFA-DPPYs) were synthesized by introducing a functional sulfonamide into the C-2 aniline moiety of pyrimidine template, and then were biologically evaluated as potent Bruton's tyrosine kinase (BTK) inhibitors. Among these molecules, inhibitors 10c, 10i, 10j and 10k displayed high potency against the BTK enzyme, with IC50 values of 1.18?nM, 0.92?nM, 0.42?nM and 1.05?nM, respectively. In particular, compound 10c could remarkably inhibit the proliferation of the B lymphoma cell lines at concentrations of 6.49?μM (Ramos cells) and 13.2?μM (Raji cells), and was stronger than the novel agent spebrutinib. In addition, the inhibitory potency toward the normal PBMC cells showed that inhibitor 10c possesses low cell cytotoxicity. All these explorations indicated that molecule 10c could serve as a valuable inhibitor for B-cell lymphoblastic leukemia treatment.
- Liu, He,Qu, Menghua,Xu, Lina,Han, Xu,Wang, Changyuan,Shu, Xiaohong,Yao, Jihong,Liu, Kexin,Peng, Jinyong,Li, Yanxia,Ma, Xiaodong
-
-
- An eco-friendly tandem tosylation/Ferrier N-glycosylation of amines catalyzed by Er(OTf)3 in 2-MeTHF
-
Er(OTf)3 in 2-MeTHF provides a new and eco-friendly process for Ferrier glycosylation of sulfonamides and amino acids with various N-nucleophiles. The stereoselective synthesis of 2,3-unsaturated-N-pseudoglycals was carried out with 3,4,6-tri-O-acetyl-D-glucal and different nucleophiles affording good results in a short time.
- Nardi, Monica,Cano, Natividad Herrera,De Nino, Antonio,Di Gioia, Maria Luisa,Maiuolo, Loredana,Oliverio, Manuela,Santiago, Ana,Sorrentino, Diletta,Procopio, Antonio
-
supporting information
p. 1721 - 1726
(2017/04/13)
-
- Design, synthesis and biological evaluation of sulfonamide-substituted diphenylpyrimidine derivatives (Sul-DPPYs) as potent focal adhesion kinase (FAK) inhibitors with antitumor activity
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A class of sulfonamide-substituted diphenylpyrimidines (Sul-DPPYs) were synthesized to improve activity against the focal adhesion kinase (FAK). Most of these new Sul-DPPYs displayed moderate activity against the FAK enzyme with IC50 values of less than 100?nM; regardless, they could effectively inhibit several classes of refractory cancer cell lines with IC50 values of less than 10?μM, including the pancreatic cancer cell lines (AsPC-1, Panc-1 and BxPC-3), the NSCLC-resistant H1975 cell line, and the B lymphocyte cell line (Ramos cells). Results of flow cytometry indicated that inhibitor 7e promoted apoptosis of pancreatic cancer cells in a dose-dependent manner. In addition, it almost completely induced the apoptosis at a concentration of 10?μM. Compound 7e may be selected as a potent FAK inhibitor for the treatment of pancreatic cancer.
- Qu, Menghua,Liu, Zhihao,Zhao, Dan,Wang, Changyuan,Zhang, Jianbin,Tang, Zeyao,Liu, Kexin,Shu, Xiaohong,Yuan, Hong,Ma, Xiaodong
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p. 3989 - 3996
(2017/07/05)
-
- CuI catalyzed sulfamidation of arylboronic acid using TsNBr2 at room temperature
-
An expeditious protocol for amidation arylboronic acid has been developed using TsNBr2 as the nitrogen source in presence of a CuI as catalyst. Various arylboronic acids could be transformed into corresponding N-arylsulfonamide derivatives within a very short time using CuI as catalyst in presence of DBU at room temperature.
- Loukrakpam, Dineshwori Chanu,Phukan, Prodeep
-
supporting information
p. 4855 - 4858
(2017/11/29)
-
- Copper-Catalyzed Direct Nitration on Aryl C-H Bonds by Concomitant Azidation-Oxidation with TMS Azide and TBHP under Aerobic Conditions
-
An unprecedented copper-catalyzed in situ azidation-oxidation for the nitration of anilides and sulfonamides has been developed by direct CAr-H functionalization. This novel and efficient nitration protocol is achieved employing TMSN3 and TBHP without the exclusion of air or moisture. The synthetic applications of the 2-nitroanilides have been explored.
- Vinayak, Botla,Chandrasekharam, Malapaka
-
supporting information
p. 3528 - 3531
(2017/07/17)
-
- Sustainable synthesis of sulfonamides using supported ionic liquid phase catalyst containing Keggin-type anion
-
A silica-supported ionic liquid phase catalyst containing Keggin-type anion has been prepared by covalent grafting of ferrocene-tagged ionic liquid in a matrix of silica followed by anion metathesis reaction. This novel catalyst served as a robust heterogeneous catalyst for the synthesis of biologically active sulfonamides from 4-toluenesulfonyl chloride and amines. Additionally, recycling experiments showed that the catalyst could be reused five times.
- Jagadale, Megha,Khanapure, Sharanabasappa,Salunkhe, Rajashri,Rajmane, Mohan,Rashinkar, Gajanan
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p. 125 - 131
(2016/02/14)
-
- An efficient practical tosylation of phenols, amines, and alcohols employing mild reagent [DMAPTs]+Cl?
-
Efficient exploration of [DMAPTs]+Cl?for base free and chromatography free preparation of sulfonate esters from phenols and alcohols and sulfonamides from amines was achieved in excellent yields. Majority of the phenols irrespective of their substituents electronic nature underwent tosylation nearly at same reaction rate with an average yield of 95%. For amines, ring activating substituents favors rapid sulfonylation while the ring deactivating substituents relatively lowers the rate of tosylation. Furthermore the reagent was employed for Chemoselective sulfonylation as well as solvent free tosylation of phenols and amines.
- Dhonthulachitty, Chiranjeevi,Kothakapu, Sridhar Reddy,Neella, Chandra Kiran
-
supporting information
p. 4620 - 4623
(2016/09/23)
-
- Palladium nanoparticles as reusable catalyst for the synthesis of N-aryl sulfonamides under mild reaction conditions
-
An efficient palladium nanoparticles-catalyzed N-arylation of sulfonamides and sulfonyl azides is described. This procedure serves as an active protocol for intermolecular C-N bond formation using Pd(OAc)2 in PEG-400 under air. Aryl bromides and triflates react at 35°C, while aryl chlorides require heating to 50°C and give the desired products only in low yields. This reaction proceeds smoothly in acceptable yields using low catalyst loading.
- Khalaj, Mehdi,Ghazanfarpour-Darjani, Majid,Talei Bavil Olyai, Mohamad Reza,Shamami, Sakineh Faraji
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p. 211 - 221
(2016/03/30)
-
- Aqueous MW eco-friendly protocol for amino group protection
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In this paper a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride is presented. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambident nucleophiles and water solution of di-tert-butyl carboxylic acid or chloride acid are the only wastes produced.
- Nardi,Cano, N. Herrera,Costanzo,Oliverio,Sindona,Procopio
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p. 18751 - 18760
(2015/06/15)
-
- Ultrasound-promoted green approach for the synthesis of sulfonamides using natural, stable and reusable Natrolite nanozeolite catalyst at room temperature
-
Natural Natrolite nanozeolite has been investigated as an efficient and reusable catalyst for the N-sulfonylation of amines under ultrasound irradiation at room temperature. Compared with traditional methods, the significant advantages for method are green solvent, milder and cleaner conditions, higher purity and yields, shorter reaction time, easier work-up procedure and the lower generation of waste or pollutions. The catalyst can be recovered and reused several times without significant loss of its catalytic activity.
- Nasrollahzadeh, Mahmoud,Ehsani, Ali,Rostami-Vartouni, Akbar
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p. 275 - 282
(2013/10/01)
-
- Palladium-catalyzed intramolecular oxidative coupling involving double C(sp2)-H bonds for the synthesis of annulated biaryl sultams
-
The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.
- Laha, Joydev K.,Jethava, Krupal P.,Dayal, Neetu
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p. 8010 - 8019
(2015/03/18)
-
- Direct oxidative nitration of aromatic sulfonamides under mild conditions
-
A direct nitration of aromatic sulfonamides using sodium nitrite as the nitrating agent has been developed. The reaction shows typically mono-substitution selectivity and can be enlarged to the gram scale with good yield.
- Li, Ying-Xiu,Li, Lian-Hua,Yang, Yan-Fang,Hua, Hui-Liang,Yan, Xiao-Biao,Zhao, Lian-Biao,Zhang, Jin-Bang,Ji, Fa-Jin,Liang, Yong-Min
-
supporting information
p. 9936 - 9938
(2014/08/18)
-
- Copper-catalyzed mild nitration of protected anilines
-
A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.
- Hernando, Elier,Castillo, Rafael R.,Rodríguez, Nuria,G?mez Arrayás, Ram?n,Carretero, Juan C.
-
supporting information
p. 13854 - 13859
(2016/02/18)
-
- Combustion-derived CdO nanopowder as a heterogeneous basic catalyst for efficient synthesis of sulfonamides from aromatic amines using p-toluenesulfonyl chloride
-
A simple and rapid synthesis of CdO nanopowder via the solution combustion route employing l-(+)-tartaric acid as a fuel is reported for the first time. The catalyst was characterized by PXRD, SEM, TEM, BET surface area measurement, basic site measurement from back titration and FTIR. Combustion derived CdO nanopowder acts as a catalyst in the sulfonylation of amines with p-toluenesulfonyl chloride to obtain sulfonamides in excellent yield (85-95 %) and high purity under mild reaction conditions. CdO nanopowder has been found to be an efficient catalyst requiring a shorter reaction time (10-30 min) to obtain sulfonamide when compared with the commercial CdO powder requiring 2 h under similar conditions. The catalyst can be recovered and reused four times without any significant loss of catalytic activity. Potential role of CdO nanopowder in the synthesis of sulfonamides and its mechanism is proposed.
- Anandakumar, Belladamadu Siddappa,Madhusudana Reddy, Muthukur Bhojegowd,Thipperudraiah, Kumarappa Veerappa,Pasha, Mohamed Afzal,Chandrappa, Gujjarahalli Thimmanna
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p. 135 - 144
(2013/06/04)
-
- Chemoselective nitration of aromatic sulfonamides with tert-butyl nitrite
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A methodology for the efficient conversion of aromatic sulfonamides into their mono-nitro derivatives using tert-butyl nitrite is reported. The reaction exhibits a high degree of chemoselectivity for sulfonamide functionalized aryl systems, even in the presence of other sensitive or potentially reactive functionalities.
- Kilpatrick, Brenden,Heller, Markus,Arns, Steve
-
supporting information
p. 514 - 516
(2013/02/25)
-
- Sulfapyridine-like benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI
-
The inhibition of two human cytosolic carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I, II and human serum isozyme VI, with a series of tosylited aromatic amine derivatives was investigated. The KI ranges of compounds 1-14 and acetazolamide against hCA I ranged between 1.130 and- 448.2 μM, against hCA II between 0.103 and- 14.3 μM, and against hCA VI ranged between 0.340 and- 42.39 μM. Tosylited aromatic amine derivatives are thus interesting hCA I, II and VI inhibitors, and might be used as leads for generating enzyme inhibitors eventually targeting other isoforms which have not been assayed yet for their interactions with such agents.
- Alp, Cemalettin,?zsoy, ?eyda,Alp, Nurdan Alcan,Erdem, Deryanur,Gültekin, Mehmet Serdar,Küfrevio?lu, ?mer Irfan,?entürk, Murat,Supuran, Claudiu T.
-
p. 818 - 824
(2013/02/23)
-
- Nanocopper-mediated direct arylsulfonamidation of aryl halides with arylsulfonyl azides
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An efficient protocol for direct arylsulfonamidation of aryl iodides and aryl bromides using arylsulfonylazides catalyzed by copper nanoparticles is described. Iranian Chemical Society 2012.
- Yavari,Solgi,Ghazanfarpour-Darjani,Ahmadian
-
p. 977 - 981
(2013/02/23)
-
- Ionic liquid-supported synthesis of sulfonamides and carboxamides
-
An ionic liquid-supported aldehyde was designed and converted to ionic liquid-supported secondary aryl amines through reductive amination. The reaction of ionic liquid-supported aryl amines with sulfonyl chlorides and acid chlorides, respectively, followed by cleavage using trifluoroacetic acid (TFA) afforded sulfonamides and caboxamides. To introduce additional diversity in the synthesis of sulfonamides and caboxamides, ionic liquid-supported iodosubstituted aryl amine was synthesized using the same strategy, and underwent Suzuki coupling reaction, followed by reaction with a methanesulfonyl chloride to generate the corresponding biaryl sulfonamide. The advantages of the protocol over solid-phase synthesis are homogeneous reaction medium, high loading, easy separation of products, and characterization of intermediates.
- Muthayala, Manoj Kumar,Chhikara, Bhupender S.,Parang, Keykavous,Kumar, Anil
-
experimental part
p. 60 - 65
(2012/02/04)
-
- Cs2CO3 catalyzed rapid and efficient conversion of amines into sulfonamides; Alcohols and phenols into sulfonic esters
-
A simple and efficient method has been developed for the sulfonylation of several amines, alcohols, and phenols by p-toluenesulphonylchloride (p-TsCl) in the presence of catalytic amount of Cs2CO3 at 25C to obtain sulfonamides and sulfonic esters in very good yields. Cs2CO3 has been found to be highly efficient catalyst. Taylor & Francis Group, LLC.
- Reddy, M. B. Madhusudana,Pasha
-
experimental part
p. 1867 - 1875
(2011/10/11)
-
- CsF-Celite as an efficient heterogeneous catalyst for sulfonylation and desulfonylation of heteroatoms
-
CsF-Celite is found to be as an efficient reusable catalyst for sulfonylation and desulfonylation of heteroatoms. Sulfonamides and N-acylsulfonamides deprotect efficiently in the presence of CsF-Celite under solvent free conditions to give the free amines or amides in good to excellent yields.
- Tamaddon, Fatemeh,Nasiri, Alireza,Farokhi, Somayeh
-
experimental part
p. 1477 - 1482
(2012/06/18)
-
- A green, catalyst-free method for the synthesis of sulfonamides and sulfonylazides
-
A novel, green method for the efficient synthesis of sulfonamide and sulfonylazide derivatives by the reaction of sulfonyl chlorides with amines or sodium azide under catalyst-free conditions has been developed. The reactions proceed with high yields and excellent selectivities in short reaction times. Copyright Taylor & Francis Group, LLC.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Golshani, Tayebeh
-
experimental part
p. 140 - 148
(2011/04/22)
-
- Copper-catalysed N-arylation of arylsulfonamides with aryl bromides and aryl iodides using KF/Al2O3
-
An efficient synthesis of N-arylsulfonamides with a variety of aryl bromides, aryl iodides and heteroaryl bromides using KF/Al2O 3 as a suitable base, CuI as an inexpensive catalyst and N,N′dimethylethylenediamine (N,N′-DMEDA) as an effective ligand is described. Indian Academy of Sciences.
- Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Alikarami, Mohammad
-
experimental part
p. 143 - 148
(2010/11/16)
-
- A simple and efficient method for sulfonylation of amines, alcohols and phenols with cupric oxide under mild conditions
-
Cupric Oxide efficiently catalyzed the synthesis of sulfonamides and sulfonic esters. This method has been applied to a variety of substrates including nucleophilic and sterically-hindered amines, alcohols and phenols with excellent yields of sulfonamides and sulfonic esters. The remarkable selectivity under mild and neutral conditions of this commercially available inexpensive catalyst is an attractive feature of this method.
- Meshram,Patil, Vishvanath D.
-
scheme or table
p. 1117 - 1121
(2009/05/27)
-
- CuO nanoparticles catalyzed C-N, C-O, and C-S cross-coupling reactions: Scope and mechanism
-
CuO nanoparticles have been studied for C-N, C-O, and C-S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs 2CO3, and K2CO3 at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.
- Jammi, Suribabu,Sakthivel, Sekarpandi,Rout, Laxmidhar,Mukherjee, Tathagata,Mandai, Santu,Mitra, Raja,Saha, Prasenjit,Punniyamurthy, Tharmalingam
-
supporting information; experimental part
p. 1971 - 1976
(2009/07/01)
-
- Mild and efficient indium metal catalyzed synthesis of sulfonamides and sulfonic esters
-
A facile and efficient method for synthesizing sulfonamides was developed using a catalytic amount of indium metal. A wide range of sulfonamides were synthesized in excellent yields using the new process. The method showed a generality for substrates including less nucleophilic and sterically hindered anilines, and it is also applicable for preparing sulfonic esters from sulfonyl chlorides and alcohols. Georg Thieme Verlag Stuttgart.
- Kim, Joong-Gon,Doo, Ok Jang
-
p. 2501 - 2504
(2008/02/13)
-
- A practical, water-soluble, ionic scavenger for the solution-phase syntheses of amides
-
A new ionic, water-soluble scavenger for acyl chlorides, 1-(2-aminoethyl)pyridinium bromide (1), has been investigated. Compound 1 was used for the rapid and simple purification of a series of benzamides and sulfonamides (Table) obtained by solution-phase synthesis from the corresponding amines (Scheme). The inexpensive scavenger, which can be prepared on large scale, was shown to readily 'eliminate' excess acyl chlorides (reagent) by simple aqueous extraction. The amides purified in this way were obtained in excellent yields and purities (Table), which makes 1 a versatile new reagent, especially for the combinatorial solution-phase synthesis of amide libraries.
- Lei, Ming,Tao, Xiao-Le,Wang, Yan-Guang
-
p. 532 - 536
(2007/10/03)
-
- Effect of para substitution on dissociation of N-phenylbenzenesulfonamides
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The reaction of substituted anilines and benzenesulfonyl chlorides has been used to prepare 49 substituted N-phenylbenzenesulfonamides of general formula 4-X-C6H4SO2NHC6H4-Y- 4′. Their purity was checked by elemental analysis. The substituents X and Y include H, CH3, CH3O, Cl, Br, CN, and NO2. The dissociation constants of all compounds were determined by potentiometric titration in methanol, acetonitrile, N,N-dimethylformamide, and pyridine. The obtained dissociation constants, pKHA, were correlated with various sets of substituent constants. It was found that the effects of substituents X and Y on the dissociation are best described by using the Hammett equation with σp constants and the Yukawa-Tsuno equation with σp- and σp constants, respectively. This result confirms the direct conjugation of Y substituent with the reaction centre. The explained variability using the additive model was above 96% in all the solvents used. The data also provided information about the transmission effect of the SO2 group. The average dissociation constants were further processed by the latent variables methods, principal components and conjugated deviations analyses.
- Mansfeld, Martin,Parik, Patrik,Ludwig, Miroslav
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p. 1479 - 1490
(2007/10/03)
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- Synthesis of nonracemic 9-(1-methoxycarbonylethyl)-1,2,3,4-tetrahydrocarbazole
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A new approach has been proposed to the synthesis of indole derivatives containing a chiral substituent at the nitrogen atom, comprizing Fischer indolization of phenylhydrazines with a chiral substituent at the α-nitrogen atom. The initial hydrazines were obtained by the alkylation (Mitsunobu reaction applying optically active esters of lactic acid) of anilines containing an electron-accepting substituent at the amino group. Subsequent removal of the activating acceptor grouping was realized by nitrosation of the chiral secondary aniline followed by reduction of the corresponding N-nitroso compound.
- Kurkin,Nesterov,Karchava,Yurovskaya
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p. 1466 - 1477
(2007/10/03)
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- Antifungal activities of N-arylbenzenesulfonamides against phytopathogens and control efficacy on wheat leaf rust and cabbage club root diseases.
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A set of N-arylbenzenesulfonamides with various substituents at the arylamine and benzenesulfonyl positions were prepared, and their antifungal properties were measured in vitro against such plant pathogenic fungi as Pythium ultimum, Phytophthora capsici, Rhizoctonia solani, and Botrytis cinerea. Compounds 3, 4, 8, 9, 10, 14, 16, 18, 20, 21, 24 and 27 had antifungal activity over a broad spectrum of the phytopathogenic fungi tested, where 50% of inhibition (ED50) was in the range of 3-15 microg/ml. Based on the in vitro activity, six derivatives (3, 4, 10, 18, 21 and 27) were selected and tested further for their fungicidal efficacy in vivo. The fungicidal efficacy of 10, 21 and 27 had a disease control value of over 85% at 50 microg/ml against wheat leaf rust, while that of 4 was selective against cabbage club root disease.
- Kang, Jae Gon,Hur, Jong Hyun,Choi, Sung Jun,Choi, Gyung Ja,Cho, Kwang Yun,Ten, Leonid N,Park, Ki Hun,Kang, Kyu Young
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p. 2677 - 2682
(2007/10/03)
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- Samarium(0) and 1,1′-dioctyl-4,4′-bipyridinium dibromide: A novel electron-transfer system for the chemoselective reduction of aromatic nitro groups
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A mild and efficient electron-transfer method was developed for the chemoselective reduction of aromatic nitro groups using samarium(0) metal in the presence of a catalytic amount of 1,1′-dioctyl-4,4′-bipyridinium dibromide. This method was found to give the product aromatic amine in 79-99% yield with selectivity over a number of other functional and protecting groups such as alkene, azide, benzyl ether, nitrile, amide, halide, p-toluenesulfonamide, t-Boc, tert-butyldiphenylsilyl ether, and aliphatic nitro groups. Our results also indicate that samarium(0) plays an important role in the reduction process and that 1,1′-dioctyl-4,4′-bipyridinium dibromide acts as an electron-transfer catalyst and is essential in the activation of samarium(0) metal. The major active reducing agent responsible for the reduction is believed to be the radical cation species formed from 1,1′-dioctyl-4,4′-bipyridinium dibromide.
- Yu,Liu,Hu
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p. 919 - 924
(2007/10/03)
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- Solid phase synthesis of sulfonamides using a carbamate linker
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A method for the synthesis of sulfonamides on a solid support by immobilizing amines through the nitrogen atom using a carbamate linkage is described.
- Raju,Kogan, Timothy P.
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p. 3373 - 3376
(2007/10/03)
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- Use of halomethyl resins to immobilize amines: An efficient method for synthesis of sulfonamides and amides on a solid support
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Methods for the synthesis of chloromethyl and bromomethyl equivalents of Wang's resin are described. To explore the utility of this acid clearable resin, amines were immobilized through the nitrogen atom, further functionalized, and then cleaved under acid conditions.
- Raju,Kogan, Timothy P.
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p. 4965 - 4968
(2007/10/03)
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