112111-43-0Relevant articles and documents
Vanadium–Schiff base complex-functionalized SBA-15 as a heterogeneous catalyst: synthesis, characterization and application in pharmaceutical sulfoxidation of sulfids
Taghizadeh, Mohammad Javad,Karimi, Homman,Abandansari, Hamid Sadeghi
, p. 8201 - 8215 (2016)
VO2(picolinichydrazone) complex as a catalyst was stabilized on a SBA-15 mesoporous silica as a catalytic support by using (3-chloropropyl)triethoxysilane as a connector. SBA-15 is nanoporous and has a high ratio of surface area to volume. The immobilization of a metal–Schiff base complex to the surface area of SBA-15 can improve its catalytic effects by increasing the catalytic surface area. Unlike homogeneous catalysts, heterogeneous catalysts can be recovered and reused several times without any significant loss of catalytic activity. A vanadium–Schiff base complex-functionalized SBA-15 was synthesized by covalency connected by a pre-synthesised VO2(picolinichydrazone) complex to silanated SBA-15. The synthesized vanadium–Schiff base complex was characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy, carbon nuclear magnetic resonance (13C NMR) spectroscopy and Fourier transform infrared spectroscopy (FT-IR), and the final V/SBA-15 was characterized by FT-IR, ultraviolet–visible spectrophotometry and X-ray powder diffraction. The morphology of V/SBA-15 was also obtained by scanning electron microscopy and transmission electron microscopy. The catalytic effect was examined by using V/SBA-15 as a heterogeneous catalyst in sulfoxidation reactions. The synthesis of modafinil and modafinic acid by pharmaceutical sulfoxidation of solfides was carried out and the effects of different solvents, reaction times and also recoverability and reusability of the heterogeneous catalyst were investigated. This catalyst showed high yield of sulfide conversion, stability and recyclability in the sulfoxidation of sulfides.
New synthetic route to modafinil drug including desulfobenzhydrylation of sodium carbamoylmethyl thiosulfate: Experimental and quantum chemical studies
Bicherov,Akopova,Spiglazov,Morkovnik
, p. 91 - 101 (2010)
A new synthetic route to 2-benzhydrylsulfinylacetamide (1), a nootropic drug modafinil, is described. The synthesis includes the alkylation of sodium thiosulfate with chloroacetamide to sodium carbamoylmethyl thiosulfate, the desulfobenzhydrylation of the latter by benzhydrol in formic acid to form benzhydrylthioacetamide (3a), and the further oxidation of this thioamide with hydrogen peroxide. According to B3LYP/6-31G** DFT calculations, the key step of the synthesis, namely, desulfobenzhydrylation of salt 6a, occurs only insignificantly due to the energetically unfavorable direct attack of this salt by benzhydryl formate; the reaction mainly involves the attack by the benzhydrilium carbocation Ph2CH+. The oxidation of sulfide 3a to sulfinylacetamide 1 is efficiently catalyzed by side proton-donor molecules (constituents of the transition states of the reaction). The oxidant can be the anionic form of the reactant (HO2- ion), which reacts with sulfide 3a via the unusual noncatalytic mechanism. At the step of transition state formation, this mechanism resembles the S N2 substitution.
Self-repairing metal-organic hybrid complexes for reinforcing immobilized chloroperoxidase reusability
Liu, Yan,Zhang, Yumei,Li, Xuejian,Yuan, Qipeng,Liang, Hao
, p. 3216 - 3219 (2017)
A self-repairing metal-enzyme hybrid nanocatalyst with a sodium alginate (SA) coating was reported in this study. Compared with free CPO, immobilized chloroperoxidase (CPO) has similar Km and Kcat values. SA-coated CPO@Ca3
Microbial oxidation/amidation of benzhydrylsulfanyl acetic acid. Synthesis of (+)-modafinil
Olivo, Horacio F.,Osorio-Lozada, Antonio,Peeples, Tonya L.
, p. 3507 - 3511 (2005)
A highly enantioselective oxidation of benzhydrylsulfanyl acetic acid to the corresponding (S)-sulfinyl carboxylic acid was achieved employing the fungus Beauveria bassiana in very good yield. This product was amidated using the bacteria Bacillus subtilis to afford (S)-modafinil in good yield.
One-pot parallel synthesis of alkyl sulfides, sulfoxides, and sulfones
Bogolubsky, Andrey V.,Moroz, Yurii S.,Mykhailiuk, Pavel K.,Ostapchuk, Eugeniy N.,Rudnichenko, Alexander V.,Dmytriv, Yurii V.,Bondar, Anna N.,Zaporozhets, Olga A.,Pipko, Sergey E.,Doroschuk, Roman A.,Babichenko, Liudmyla N.,Konovets, Anzhelika I.,Tolmachev, Andrey
, p. 348 - 354 (2015)
A simple and cost-effective one-pot parallel synthesis approach to sulfides, sulfoxides, and sulfones from thiourea was elaborated. The method combines two procedures optimized to the parallel synthesis conditions: alkylation of thiourea with alkyl chlorides and mono or full oxidation of in situ generated sulfides with H2O2 or H2O2-(NH4)2MoO4. The experimental set up required commonly used lab equipment: conventional oven and ultrasonic bath; the work up includes filtration or extraction with chloroform. The method was evaluated on an 81 member library of drug-like sulfides, sulfoxides, and sulfones yielding the compounds on a 30-300 mg scale. A small-scale synthesis of 2-(benzhydrylsulfinyl)acetamide (modafinil) utilizing our approach resulted in similar efficiency to the published procedures.
Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations
Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo
supporting information, p. 7738 - 7744 (2021/05/07)
Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.
Alloxan-catalyzed biomimetic oxidations with hydrogen peroxide or molecular oxygen
Zhang, Shiqi,Li, Guangxun,Li, Ling,Deng, Xiongfei,Zhao, Gang,Cui, Xin,Tang, Zhuo
, p. 245 - 252 (2019/12/24)
Inspired by biological flavin catalysis, the nonionic alloxan derivatives were applied as the biomimetic catalysts for various oxidations, catalyzing oxidations of sulfides and amines with hydrogen peroxide or molecular oxygen under mild conditions with high yields in a short time. The whole catalytic cycle has been verified to be a biomimetic approach through the formation of the alloxan hydroperoxide reactive intermediate. Additionally, encouraging asymmetric catalytic results have been obtained with an easily prepared chiral alloxan in a sulfoxidation reaction.