22057-44-9Relevant academic research and scientific papers
Primary sulfonamide as a coupling partner: Copper(I)-catalyzed regioselective cross-coupling of 2-nitro benzenesulfonamides with thiol through the cleavage of Ar–SO2NH2 bonds
Chen, Junmin,Zhang, Kuo,Zhao, Yongli,Pu, Shouzhi
, p. 1316 - 1323 (2018/04/05)
In this article, we have presented a novel and efficient method for the direct synthesis of unsymmetrical sulfides through the copper(I)-catalyzed cross-coupling of 2-nitro benzenesulfonamides with thiols in the presence of catalytic amount of CuI in DMF as solvent at 100 °C. In addition, the products were obtained in high to excellent yields. More importantly, the novel system showed the primary 2-nitro benzenesulfonamides as a new coupling partner and regioselectively promoted C–S bond-forming transformations through the cleavage of Ar–SO2NH2 bonds.
The invention relates to a thiourea as the sulfur source synthesis of substituted 2 - aryl benzo thiazole
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Paragraph 0019, (2017/08/25)
The invention discloses a method for synthesizing poly-substituted 2-aryl benzothiazoles by utilizing thiourea as a sulphur source. According to the method, thiourea reacts with benzyl chloride to generate an S-benzylisothiourea salt in situ. After that, through the aromatic nucleophilic substitution reaction of the obtained S-benzylisothiourea salt with 2-fluoronitrobenzene and then the one-step reduction (one-pot reaction) process, o-amino phenyl benzyl thioether as an intermediate product can be obtained. Finally, through the iron-catalyzed cross-dehydrogenative-coupling reaction of the o-amino phenyl benzyl thioether, a target product can be obtained. Compared with the traditional synthetic method, the method has the significant advantages of (1) short reaction step, wherein the target product can be synthesized through only three steps of simple reactions by utilizing simple chemical raw materials; (2) mild reaction condition, high atom economy, and relatively safe and cheap reaction reagents; (3) high reaction yield, good substrate tolerance and free of any dangerous or high-toxicity reagent. Therefore, the method might be applied to the large-scale production.
Histidine-functionalized chitosan-Cu(II) complex: A novel and green heterogeneous nanocatalyst for two and three component C-S coupling reactions
Hajipour, Abdol Reza,Hosseini, Seyed Mostafa,Jajarmi, Saeideh
, p. 7447 - 7452 (2017/08/01)
Using a fixing Cu2+ NP reaction on histidine modified chitosan, a novel applicable matrix was successfully prepared and investigated as a heterogeneous nanocatalyst for preparing diaryl sulfides and aryl benzyl thioethers. The Cu(ii)-his@CS nanocatalyst was characterized by FT-IR, CHN, XRD, FE-SEM, TEM, EDX, ICP-AES and TG analysis. This novel copper nanocatalyst was used for two and three component C-S coupling reactions of different aryl halides. The nanocatalyst showed high catalytic activity and reusability in both reactions.
Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction
Zhang, Xiao,Lu, Guo-Ping,Cai, Chun
, p. 5580 - 5585 (2016/10/21)
A facile aromatic nucleophilic substitution (SNAr) reaction in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments, 1H NMR and IR spectroscopies. This chemistry provides an efficient and metal-free approach for the generation of Caryl-X (XS, N, O) bonds, many of which are significant synthetic intermediates or drugs, making this methodology attractive to both synthetic and medicinal chemistry.
An odorless, one-pot synthesis of nitroaryl thioethers via SNAr reactions through the in situ generation of S-alkylisothiouronium salts
Lu, Guo-Ping,Cai, Chun
, p. 59990 - 59996 (2015/02/19)
A newly developed C-S bond formation nucleophilic aromatic substitution (SNAr) reaction in aqueous Triton X-100 (TX100) micelles has been disclosed. This chemistry, in which odorless, cheap and stable thiourea in place of thiols is used as the sulfur reagent, provides an efficient approach for the generation of nitroaryl thioethers, which are useful structural units of many bioactive molecules, rendering this methodology attractive to both synthetic and medicinal chemistry.
Nickel-Schiff base complex catalyzed C-S cross-coupling of thiols with organic chlorides
Gogoi, Prasanta,Hazarika, Sukanya,Sarma, Manas J.,Sarma, Kuladip,Barman, Pranjit
, p. 7484 - 7489 (2014/12/10)
We report an efficient, mild and convenient synthetic protocol for the C-S cross-coupling reaction of various aryl, benzyl, allyl chlorides and thiols using 5 mol % Nickel-Schiff base catalyst with NaOH as the base, in DMF at 70 °C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available organic chlorides and thiols.
An efficient protocol for the carbon-sulfur cross-coupling of sulfenyl chlorides with arylboronic acids using a palladium catalyst
Gogoi, Prasanta,Kalita, Mukul,Barman, Pranjit
, p. 866 - 870 (2014/04/03)
An efficient protocol for carbon-sulfur bond formation is developed, which involves the cross-coupling of sulfenyl chlorides and arylboronic acids catalyzed by a novel palladium-Schiff base complex. Good to high product yields, short reaction times, and mild reaction conditions are important features of this new method. Georg Thieme Verlag Stuttgart · New York.
Synthesis and biological evaluation of nonsymmetrical aromatic disulfides as novel inhibitors of acetohydroxyacid synthase
Li, Zai-Shun,Wang, Wei-Min,Lu, Wei,Niu, Cong-Wei,Li, Yong-Hong,Li, Zheng-Ming,Wang, Jian-Guo
supporting information, p. 3723 - 3727 (2013/07/25)
46 Novel nonsymmetrical aromatic disulfides containing [1,3,4]thiadiazole or [1,3,4]oxadiazole groups were synthesized and their biological activities were evaluated as inhibitors of acetohydroxyacid synthase (AHAS, EC 2.2.1.6). Besides their strong in vitro inhibition against plant AHAS, compounds 3e and 3f also display 80-100% post-emergence herbicidal activities in greenhouse bioassay at 1500 g/ha dosage. The assay of exogenous branched-chain amino acids supplementation on rape root growth of 3e suggests that the herbicidal activity has relationship with AHAS inhibition.
Synthesis and evaluation of novel sulfenamides as novel anti Methicillin-resistant Staphylococcus aureus agents
Shang, Jian-Li,Guo, Hui,Li, Zai-Shun,Ren, Biao,Li, Zheng-Ming,Dai, Huan-Qin,Zhang, Li-Xin,Wang, Jian-Guo
supporting information, p. 724 - 727 (2013/02/25)
A total of 29 novel sulfenamide compounds were synthesized, spectroscopically characterized and evaluated in vitro for antimicrobial activity against various infectious pathogens. Compounds 1b and 2c exhibited potent inhibition against clinical Methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentration (MIC) values of 1.56 μg/mL.
Silver ion mediated in situ synthesis of mixed diaryl sulfides from diaryl disulfides
Gogoi, Prasanta,Gogoi, Sandhya R.,Kalita, Mukul,Barman, Pranjit
, p. 873 - 877 (2013/05/21)
The AgNO3-mediated in situ scission of aromatic disulfides in the presence of electron-rich aromatic compounds results in the efficient synthesis of diaryl sulfides. Key features of this new methodology are high yields of aromatic and heteroaromatic sulfides, mild reaction conditions, simplicity, simple workup, and avoiding foul-smelling reactants like thiols. Georg Thieme Verlag Stuttgart · New York.
