1155-00-6Relevant academic research and scientific papers
Bromonitromethane, a Versatile Electrophile: Reactions with Thiolates
Fishwick, Brian R.,Rowles, David K.,Stirling, Charles J. M.
, p. 834 - 835 (1983)
Thiolate ions react with bromonitromethane to give nitronate ion and, initially, sulphenyl bromide which reacts with further thiolate ion to give disulphide; when the disulphide bears an appropriately placed nitrile function, intramolecular attack by the nitronate ion at this function and subsequent intramolecular displacement of thiolate ion yields aminothiophenes.
Synthesis and structural study of 1-(N,N-diethylamino)-2,2-bis(2-nitrophenylthio)ethene
Aupers, John H.,Skakle, Janet M.S.,Wardell, James L.,Wardell, Solange M.S.V.
, p. 435 - 443 (2001)
The synthesis, variable temperature NMR spectra, and crystal structures of two crystalline forms, 2a and 2b, of the enamine 1-(N,N-diethylamino)-2,2-bis(2-nitrophenylthio)ethene have been obtained. Both forms crystallize in the monoclinic space group P21/a. The two phases have similar molecular structures but possess different intermolecular C - H ... O hydrogen bonding interactions. Both forms exhibit disorder within the NEt2 fragment at 298 K: sufficient disorder persisted with 2a (orange needles) down to 100 K to make the geometric parameters pertaining to the enamine fragment unreliable. The disorder was effectively eliminated on cooling 2b down (red colored blocks) to 150 K. Cell dimensions for the 2a-phase are at 100 K: a = 11.1030(4) A, b = 15.1325(7) A, c = 12.4504(7) A, β = 114.606(3)°, while for the 2b-phase at 150 K, a = 15.5206(4) A, b = 7.6958(2) A, c = 15.7137(3) A, β = 92.580(7)°. The C - N bond length in the β-form at 150 K of 1.335(3) A indicates considerable double bond character: the rotational barrier of the C - N bond in CDCl3 was calculated to be 52.4 kJ mol-1.
Using Solid Catalysts in Disulfide-Based Dynamic Combinatorial Solution- and Mechanochemistry
Belenguer, Ana M.,Lampronti, Giulio I.,Michalchuk, Adam A. L.,Sanders, Jeremy K. M.
, (2021/12/27)
It was shown for the first time that solid amines can act as catalysts for disulfide-based dynamic combinatorial chemistry (DCC) by ball mill grinding. The mechanochemical equilibrium for the two disulfide reactions studied was reached within 1–3 h using ten different amine catalysts. This contrasts with the weeks to months to achieve solution equilibrium for most solid amine catalysts at 2 %mol mol?1 concentration in a 2 mMolar disulfide dynamic combinatorial library in a suitable solvent. The final mechanochemical equilibrium was independent of the catalyst used but varied with other ball mill grinding factors such as the presence of traces of solvent. The different efficiencies of the amines tested were discussed.
Palladium-Catalyzed Picolinamide-Directed Benzylic C(sp3)?H Chalcogenation with Diaryl Disulfides and Diphenyl Diselenide
Wang, Kai,Hou, Jiahao,Zhang, Changjun,Cheng, Ke,Bai, Renren,Xie, Yuanyuan
supporting information, p. 2947 - 2952 (2020/06/17)
The first palladium-catalyzed direct benzylic C(sp3)?H chalcogenation with diaryl disulfides and diphenyl diselenide has been established. The coupling reaction proceeds between the thioether radical and palladiumcycle intermediate. Picolinamide serves as an excellent directing group for the C?H activation of benzylic C(sp3)?H and can be easily removed. The current protocol exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that palladium(IV) intermediate is probably formed during the course of the reaction. (Figure presented.).
Biocatalytic synthesis of diaryl disulphides and their bio-evaluation as potent inhibitors of drug-resistant Staphylococcus aureus
Saima,Soni, Isha,Lavekar, Aditya G.,Shukla, Manjulika,Equbal, Danish,Sinha, Arun K.,Chopra, Sidharth
, p. 171 - 178 (2019/01/04)
Staphylococcus aureus is a WHO Priority II pathogen for its capability to cause acute to chronic infections and to resist antibiotics, thus severely impacting healthcare systems worldwide. In this context, it is urgently desired to discover novel molecules to thwart the continuing emergence of antimicrobial resistance. Disulphide containing small molecules has gained prominence as antibacterials. As their conventional synthesis requires tedious synthetic procedure and sometimes toxic reagents, a green and environmentally benign protocol for their synthesis has been developed through which a series of molecules were obtained and evaluated for antibacterial activity against ESKAPE pathogen panel. The hit compound was tested for cytotoxicity against Vero cells to determine its selectivity index and time-kill kinetics was determined. The activity of hit was determined against a panel of S. aureus multi-drug resistant clinical isolates. Also, its ability to synergize with FDA approved drugs was tested as was its ability to reduce biofilm. We identified bis(2-bromophenyl) disulphide (2t) as possessing equipotent antimicrobial activity against S. aureus including MRSA and VRSA strains. Further, 2t exhibited a selectivity index of 25 with concentration-dependent bactericidal activity, synergized with all drugs tested and significantly reduced preformed biofilm. Taken together, 2t exhibits all properties to be positioned as novel scaffold for anti-staphylococcal therapy.
Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
, p. 3048 - 3055 (2019/03/21)
A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.
Orthanilic acid synthesizing method
-
Paragraph 0053; 0054; 0065; 0075; 0096; 0107, (2018/03/25)
The invention discloses an orthanilic acid synthesizing method. The method includes steps: step one, taking water as a reaction medium, mixing ortho-nitrochlorobenzene and sodium disulfide solution, and stirring at 60-90 DEG C until reaction is finished, so that bis(dinitrophenyl)disulfide is obtained; step two, taking water as a reaction medium, adding the bis(dinitrophenyl)disulfide while addingan oxidant into a reaction system, stirring at 60-90 DEG C until reaction is finished, so that aqueous solution of o-nitrobenzenesulphonic acid is obtained; step three, taking water as a reaction medium and o-nitrobenzenesulphonic acid as a reaction substrate, adding or not adding auxiliary agents, adding catalysts under conditions of 90-120 DEG C and 0.8-2.0MPa, stirring until reaction is finished, and acidizing to obtain orthanilic acid. The orthanilic acid yield of the method reaches 90% or above and increased by 20% or above as compared with that of an old process, product purity is higher than 99.5%, and great crystal form and freeness of metal ion residues are realized. The method has advantages of high economic benefits, environmental friendliness and the like.
A novel dual-nano assisted synthesis of symmetrical disulfides from aryl/alkyl halides
Devi, Namita,Hazarika, Sukanya,Gogoi, Prasanta,Barman, Pranjit
supporting information, p. 1927 - 1938 (2018/07/21)
Here, we have reported a novel approach towards dual-nano assisted synthesis of disulfides from coupling of alkyl/aryl halides and sulfur nanoparticles. The indium oxide nanoparticles as catalyst expedite the conversion and sulfur nanoparticle notably enhances the miscibility, providing a faster, high yielding and cost-effective process in ethanol-water system. The method has synthetic advantages in terms of mild reaction framework, catalyst regeneration, and absence of any sulfide or polysulfide linkage as by-product leading to a column free synthesis. A variety of alkyl, aryl and heteroaryl symmetrical disulfides are obtained in good to excellent yields up to exceeding 98%.
Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties
Wang, Bao-Lei,Shi, Yan-Xia,Zhang, Shu-Jun,Ma, Yi,Wang, Hong-Xue,Zhang, Li-Yuan,Wei, Wei,Liu, Xing-Hai,Li, Yong-Hong,Li, Zheng-Ming,Li, Bao-Ju
, p. 167 - 178 (2016/04/26)
A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 γ1/4g/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.
Bovine serum albumin triggered waste-free aerobic oxidative coupling of thiols into disulphides on water: An extended synthesis of bioactive dithiobis(phenylene)bis(benzylideneimine) via sequential oxidative coupling-condensation reactions in one pot from aminothiophenol and benzaldehyde
Saima,Lavekar, Aditya G.,Kumar, Rajesh,Sinha, Arun K.
, p. 113 - 123 (2015/04/14)
Bovine serum albumin (BSA) has been explored for aerobic oxidative coupling of thiols (aromatic, heterocyclic as well as aliphatic) "on water" towards formation of disulphides (SS) without using any metal/non-metal complexes, bases and additives, which renders the process environmentally benign and economically attractive with good recyclability (up to four cycles). The developed green protocol was further extended for synthesis of diallyldisulphide (DADS), an important constituent of natural occurring allicin. Among various synthesized disulphides, bis(2-aminophenyl)disulphide, obtained by oxidative coupling of 2-aminothiophenol in BSA, was further utilized for condensation with benzaldehyde in the same pot thus enabling easy access to bioactive dithiobis(phenylene)bis(benzyldeneimine). This is the first example of BSA catalysed sequential (oxidation/condensation) reaction where one SS and two CN bonds are formed solely "on water."
