6310-41-4Relevant academic research and scientific papers
Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
Zhao, Bin,Hammond, Gerald B.,Xu, Bo
supporting information, (2021/09/13)
We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.
Preparation method and purification method of N-(2-(methylthio)phenyl)acetamide compound
-
Paragraph 0022, (2020/02/14)
The invention discloses a preparation method and a purification method of an N-(2-(methylthio)phenyl)acetamide compound. The steps comprise: carrying out a heating reaction by using a benzothiazole compound as a substrate, using a N,N-dimethylacetamide solution as a solvent and adding dimethyl sulfite into the substrate under the conditions of oxygen oxidation in air, alkaline conditions and catalysis of an iodine catalyst to obtain a crude product, purifying the crude product, filtering the crude product, and removing the solvent to obtain a remaining substance; carrying out silica gel columnchromatography on the remaining substance, leaching with eluent, and collecting the effluent; combining the effluent containing the product; and concentrating the combined effluent to remove the solvent, and finally carrying out vacuum drying to obtain the target product. The method of the invention has advantages of simple process flow, low cost and high yield.
Identification of MsrA homologues for the preparation of (R)-sulfoxides at high substrate concentrations
Yang, Jiawei,Wen, Yuanmei,Peng, Liaotian,Chan, Yu,Cheng, Xiaoling,Chen, Yongzheng
, p. 3381 - 3388 (2019/04/01)
Here we report a methionine sulfoxide reductase A (MsrA) homologue with extremely high substrate tolerance and a wide substrate scope for the biocatalytic preparation of enantiopure sulfoxides. This MsrA homologue which was obtained from Pseudomonas alcaliphila (named paMsrA) showed good activity and enantioselectivity towards a series of aryl methyl/ethyl sulfoxides 1a-1k, with electron-withdrawing or electron-donating substituents at the aromatic ring. Chiral sulfoxides in the R configuration were prepared with approximately 50% of yield and up to 99% enantiomeric excess through the asymmetric reductive resolution of racemic sulfoxide catalyzed by the recombinant paMsrA protein. More importantly, kinetic resolution has been successfully accomplished with high enantioselectivity (E > 200) at initial substrate concentrations up to 320 mM (approximately 45 g L-1), which represents a great improvement in the aspect of the substrate concentration for the biocatalytic preparation of chiral sulfoxides.
Sulfated choline ionic liquid-catalyzed acetamide synthesis by grindstone method
Kalla, Reddi Mohan Naidu,Lim, Jaehwa,Bae, Jaeyeong,Kim, Il
supporting information, p. 1595 - 1599 (2017/04/03)
Sulfated choline ionic liquid (SCIL) has been found to be an efficient solid acid IL catalyst for the protection of amine groups with acetic anhydride under solvent-free grindstone conditions. The attractive features of this new catalytic methodology include its sustainability, facile work-up procedure, economic viability, and biodegradability. The SCIL catalyst was characterized using infrared spectroscopy, wide-angle X-ray scattering analysis, and scanning electron microscopy with energy dispersive X-ray spectroscopy. The catalyst could be reused six times without significant loss in activity. Furthermore, no chromatographic separations were needed to obtain the desired products.
Cleavage of C-N bonds in guanidine derivatives and its relevance to efficient C-N bonds formation
Chang, Denghu,Zhu, Dan,Zou, Peng,Shi, Lei
, p. 1684 - 1693 (2015/03/30)
Efficient nonenzymatic decomposition of guanidine derivatives with high structural and functional diversity into anilide products is achieved in the presence of PdII/Cu(II) carboxylates/CO, relying on a dual C-N bonds cleavage strategy. In this decomposition process, the cooperative action of PdII species, Cu(II) carboxylates, and CO provides not only the N-acylating agents but also an initiator to trigger this C-N bonds cleavage sequence. The current results indicate that PdII/Cu(II) carboxylates/CO system provides a convenient and practical method for highly selective cleavage of unreactive C-N single bonds.
Microwave reaction of diazonium salts with nitrites
Saez, Rebeca,Dolores Otero,Batanero, Belen,Barba, Fructuoso
experimental part, p. 492 - 494 (2009/04/06)
A series of aryldiazonium tetrafluorborates dissolved in nitrites have been converted into the corresponding anilides in almost quantitative yield in 1 min by microwave irradiation. When bromoacetonitrile was used, 2,4-bis(bromophenyl) -quinazoline was formed. The reaction of malononitrile with the diazonium salt, in DMF as a solvent, afforded 2-(dimethylaminomethylene) malononitrile and phenylhydrazone propanedinitrile.
1-METHYL-BENZO[1,2,4]THIADIAZINE 1-OXIDE DERIVATIVES
-
Page/Page column 48; 52, (2009/01/20)
The invention is directed to 1-methyl-benzo[1,2,4]thiadiazine 1-oxide derivatives and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.
The unexpected formation of a 2,2′-DI(N-ethyl-acetamino)substituted diphenyl disulfane on oxidation of 3-ethyl-2-methylbenzothiazolium tetrafluoroborate
Reichardt, Christian,Erfurt, Hans-Peter,Harms, Klaus
, p. 1081 - 1092 (2007/10/03)
Attempts at the oxidation of 3-ethyl-2-methylbenzothiazolium salt 2 with a variety of oxidizing reagents did not lead to the desired isochiral S-oxide 3 or achiral S,S-dioxide 4, in some cases, however, unexpectedly to the ring-opened dimeric 2,2′-di(N-ethyl-acetamino)substituted diphenyl disulfane 5, the molecular structure of which was confirmed by x-ray analysis. The synthesis of 2-methylbenzothiazole-S,S-dioxide 14, reported by Zincke et al. in 1915, turned out to be not reproducible.
Endocyclic Nucleophilic Substitution at Tetracoordinate Sulfur(VI)
Andersen, Kenneth K.,Chumpradit, Sumalee,McIntyre, Debra J.
, p. 4667 - 4675 (2007/10/02)
A search for endocyclic nucleophilic substitution at tetracoordinate sulfur(VI), usually sulfonyl sulfur, was carried out through the use of molecules so constructed that any intramolecular substitution process was forced to proceed through four-, five-,
FUNCTIONAL GROUP OXIDATION USING SODIUM PERBORATE
McKillop, Alexander,Tarbin, Jonathan A.
, p. 1753 - 1758 (2007/10/02)
Sodium perborate in acetic acid is an effective reagent for the oxidation of anilines to nitroarenes and of sulphides to either sulphoxides or sulphones.It is also an excellent reagent for the oxidative deprotection of ketone dimethylhydrazones.Baeyer-Villiger oxidation of ketones can be carried out with sodium perborate in either trifluoroacetic acid or acetic acid/trifluoroacetic acid mixtures, and hydroquinones and certain highly substituted phenols are smoothly converted into quinones.
