54882-04-1Relevant articles and documents
Byproduct formation during the biosynthesis of spinosyn A and evidence for an enzymatic interplay to prevent its formation
Choi, Sei-hyun,Franklin, Joseph Livy,Huang, Teng-Yi,Hung, Shang-Cheng,Jeon, Byung-sun,Kim, Namho,Liu, Hung-wen,Ruszczycky, Mark W.
supporting information, (2021/11/30)
Biosynthesis of spinosyn A in Saccharopolyspora spinosa involves a 1,4-dehydration followed by an intramolecular [4 + 2]-cycloaddition catalyzed by SpnM and SpnF, respectively. The cycloaddition also takes place in the absence of SpnF leading to questions
Electrochemical oxidations of thioethers: Modulation of oxidation potential using a hydrogen bonding network
Liu, Shiwen,Chen, Bocheng,Yang, Yi,Yang, Yuhao,Chen, Qianjin,Zeng, Xiaojun,Xu, Bo
, (2019/11/28)
A highly efficient chemo-selective electrochemical oxidation of thioethers to sulfoxides and sulfones was developed. The hydrogen bonding network generated from hexafluoro-2-propanol (HFIP) and acetic acid (AcOH) plays an important role in the modulation of oxidation potential. The hydrogen bonding network complexes strongly with the sulfoxide, making it less prone to further oxidation. Therefore, thioethers can be selectively electrochemically oxidized to sulfoxides and over-oxidization could be minimized. Moreover, this modulation of oxidization via hydrogen bonding was supported by density functional theory (DFT) calculations and cyclic voltammetry experiments.
Synthesis of: N -alkylated 2-pyridones through Pummerer type reactions of activated sulfoxides and 2-fluoropyridine derivatives
Hu, Gang,Xu, Jiaxi,Li, Pingfan
, p. 4151 - 4158 (2018/06/12)
N-Alkylated 2-pyridone products were obtained in good to excellent yields through a one-pot procedure involving either normal or interrupted Pummerer reactions between triflic anhydride activated sulfoxides and 2-fluoropyridine derivatives, followed by hydrolysis. This is a rare case that uses 2-fluoropyridine as a nucleophile in Pummerer type reactions.
PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE DERIVATIVES AS PDE9 INHIBITORS
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Page/Page column 35, (2014/02/16)
A compound of the general formula (I) wherein R1 is selected from the group consisting of phenyl unsubstituted or substituted with 1 to 3 substituents selected from F, Cl, Br, I, CN, -O-C1-C3-alkyl, fluorinated -O-C1-C3-alkyl, -(CH2)mOH and 5-membered heterocyclic group with 1 or 2 heteroatoms selected from N, O and S; and 6- or 10-membered heteroaryl with 1 to 3 heteroatoms selected from O, N and S; R2 and R3 independently of each other represent H atom or straight or branched C1-C3 alkyl; R4 is selected from the group consisting of 4- to 6- membered cycloalkyl, wherein one of carbon atoms can be replaced by O atom, and which is unsubstituted or substituted with one or two halogen atoms,and straight or branched C1-C4 alkyl; Q represents a bond or C1-C3-alkylene, which can be optionally substituted by one to three C1-C3-alkyls; X is selected from the group consisting of O, NR5, and S(O)p; R5 represents H atom or C1-C3alkyl; m is 1, 2 or 3; p is 0, 1 or 2; and salts thereof, for use as a medicament, in particular for treating cognitive function disorders and neurodegenerative diseases.
Ammonium salt catalyzed oxidation of organosulfides to organosulfoxydes
Secci, Francesco,Frongia, Angelo,Piras, Pier Paolo
, p. 603 - 605 (2014/01/23)
The selective oxidation of aromatic and aliphatic organosulfides with H2O2/H2O catalyzed by metal free ammonium salts has been explored. Reactions were performed using 2.5-5 mol % of catalyst loadings, isolating the corres
Selective oxidation of bulky sulfides to sulfoxides over titanosilicates having an MWW structure in the presence of H2O2 under organic solvent-free conditions
Kon, Yoshihiro,Yokoi, Toshiyuki,Yoshioka, Masato,Uesaka, Yumiko,Kujira, Harumi,Sato, Kazuhiko,Tatsumi, Takashi
supporting information, p. 4918 - 4921 (2013/09/02)
A selective hydrogen peroxide oxidation of sulfides to sulfoxides using Ti-MWW and Ti-IEZ-MWW catalysts was developed. This reaction was carried out under organic solvent-free conditions, and the only side-product was water. Improvement of catalytic activity toward bulky sulfides will be achieved by optimization of the topology in the Ti zeolite.
Synthesis, characterization and application of nano-sized Co 2CrO4 spinel catalyst for selective oxidation of sulfides to sulfoxides
Yazdanbakhsh, Mohammad,Khosravi, Iman,Mashhoori, Mahboobeh-Sadat,Rahimizadeh, Mohammad,Shiri, Ali,Bakavoli, Mehdi
experimental part, p. 413 - 418 (2012/03/12)
The nano-sized Co2CrO4 spinel was produced for the first time by thermal decomposition of Cr-Co gel prepared by sol-gel method. It was shown that well-crystallized spinel structure is formed after calcination at 450 °C. The usual cha
Switchable palladium-catalyst reaction of bromomethyl sulfoxides, CO, and N-nucleophiles: Aminocarbonylation at Csp3 versus oxidative carbonylation of amines
Mollar, Cristian,Ramirez De Arellano, Carmen,Medio-Simon, Mercedes,Asensio, Gregorio
, p. 9693 - 9701,9 (2012/12/12)
The palladium-catalyzed reaction of α-bromomethyl sulfoxides, carbon monoxide, and N-nucleophiles follows different reaction pathways according to the catalytic system and the reaction conditions. The Pd-xantphos catalyst affords high yields of α-sulfinyl amides by an aminocarbonylation process and is the first example of this type of transformation for a nonbenzylic sp3-hybridized carbon. On the other hand, the oxidative carbonylation of amines occurs with α-bromomethyl sulfoxides, carbon monoxide, and catalytic Pd(PPh3)4 under aerobic conditions, yielding ureas and oxalamides from either primary or secondary amines. The reaction with ambident nucleophiles such as amino alcohols was highly selective and took place exclusively at the amino group despite the presence of the alcohol functionality. In parallel to the reaction paths for simple amines, amino alcohols were converted into hydroxy sulfinyl amides when the reaction was catalyzed by Pd-xantphos, while Pd(PPh3)4 catalyst afforded cyclic carbamates. The alkoxycarbonylation reaction of bromomethyl sulfoxides with simple alcohols and CO leading to the corresponding sulfinyl esters is also described.
Switchable palladium-catalyst reaction of bromomethyl sulfoxides, CO, and N-nucleophiles: Aminocarbonylation at Csp3 versus oxidative carbonylation of amines
Mollar, Cristian,Ramirez De Arellano, Carmen,Medio-Simón, Mercedes,Asensio, Gregorio
, p. 9693 - 9701 (2013/01/15)
The palladium-catalyzed reaction of α-bromomethyl sulfoxides, carbon monoxide, and N-nucleophiles follows different reaction pathways according to the catalytic system and the reaction conditions. The Pd-xantphos catalyst affords high yields of α-sulfinyl amides by an aminocarbonylation process and is the first example of this type of transformation for a nonbenzylic sp3-hybridized carbon. On the other hand, the oxidative carbonylation of amines occurs with α-bromomethyl sulfoxides, carbon monoxide, and catalytic Pd(PPh3)4 under aerobic conditions, yielding ureas and oxalamides from either primary or secondary amines. The reaction with ambident nucleophiles such as amino alcohols was highly selective and took place exclusively at the amino group despite the presence of the alcohol functionality. In parallel to the reaction paths for simple amines, amino alcohols were converted into hydroxy sulfinyl amides when the reaction was catalyzed by Pd-xantphos, while Pd(PPh3)4 catalyst afforded cyclic carbamates. The alkoxycarbonylation reaction of bromomethyl sulfoxides with simple alcohols and CO leading to the corresponding sulfinyl esters is also described.
Alumina-supported monoperphosphoric acid for selective oxidation of sulfides to sulfoxides
Lakouraj, Moslem M.,Hasantabar, Vahid
experimental part, p. 93 - 98 (2012/01/12)
Selective oxidation of aromatic and aliphatic sulfides to the corresponding sulfoxide was achieved by using POCl3/H2O2 and (alumina-supported phosphorus oxychloride)/H2O2. A versatile procedure for th
