24678-13-5Relevant academic research and scientific papers
Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds
Fu, Hua,Liu, Can,Liu, Yong,Yang, Haijun,Zhu, Xianjin
supporting information, p. 4357 - 4363 (2020/07/14)
Visible light-induced organic reactions are important chemical transformations in organic chemistry, and their efficiency highly depends on suitable photocatalysts. However, the commonly used photocatalysts are precious transition-metal complexes and elaborate organic dyes, which hamper large-scale production due to high cost. Here, for the first time, we report a novel strategy: light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds, allowing high-value-added aromatic ketones and carboxylic acids to be easily prepared in high-to-excellent yields using readily available alkyl arenes, methyl arenes and aldehydes as materials. The mechanistic investigations showed that the treatment of inexpensive and readily available sodium trifluoromethanesulfinate with oxygen under irradiation of light could in situ form a pentacoordinate sulfide intermediate as an efficient photosensitizer. The method represents a highly efficient, economical and environmentally friendly strategy, and the light and oxygen-enabled sodium trifluoromethanesulfinate photocatalytic system represents a breakthrough in photochemistry. This journal is
Organopromoted Selectivity-Switchable Synthesis of Polyketones
Liu, Jie,Hu, Kang-Fei,Qu, Jian-Ping,Kang, Yan-Biao
, p. 5593 - 5596 (2017/10/25)
In this work, an organopromoted metal-free pharmaceutical-oriented selectivity-switchable benzylic oxidation was developed, affording mono-, di-, and trioxygenation products, respectively, using oxygen as the oxidant under mild conditions. This process facilitates dioxygenation of 2,6-benzylic positions of heterocycles, which could be inhibited by heterocycle chelation to the metal cocatalysts. Enantiopure chiral ketones could also be prepared. The noninvolvement of transition metals and toxins avoids metal or hazardous residues, consequently ensuring a final-stage gram-scale synthesis of Lenperone.
Method for directly oxidizing benzyl-position C-H bond into ketone
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Paragraph 0073-0077, (2017/08/29)
The invention discloses a method for directly oxidizing a benzyl-position C-H bond into ketone, wherein aryl ethyl compounds are catalyzed and oxidized by nitrite ester; a synergistic catalytic system of free radical initiator and nitrite ester is adopted, and a catalytic system of non-metallic catalyst and oxygen is adopted, the oxidization of the C-H bond of a free radical-activated aryl side chain is simple in operation; after completing the reaction, petroleum ether/ethyl acetate at a volume ratio of (50-1):1 is used as an eluent; column chromatography separation is performed to obtain a target product. The catalytic system in the invention uses oxygen as an oxygen source and has high atomic economy; the invention is a non-metallic catalytic system and provides a novel method for avoid metal residues in synthetic drugs; for diethyl aromatic hydrocarbon, the method provided by the invention can be adopted to selectively oxidize diethyl aromatic hydrocarbon into monoketone and diketone; the method of the invention can be adopted to efficiently synthesize tranquillizer lenperone, so that a novel method for synthesizing lenperone is provided.
Iron-catalyzed oxyfunctionalization of aliphatic amines at remote benzylic C-H sites
Mbofana, Curren T.,Chong, Eugene,Lawniczak, James,Sanford, Melanie S.
, p. 4258 - 4261 (2016/09/09)
We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp3)-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.
Ketanserin Analogues: Structure-Affinity Relationships for 5-HT2 and 5-HT1C Serotonin Receptor Binding
Herndon, Jeff L.,Ismaiel, Abd,Ingher, Stacy P.,Teitler, M.,Glennon, Richard A.
, p. 4903 - 4910 (2007/10/02)
Ketanserin is the prototypic 5-HT2 serotonin antagonist; although it has been an important tool for the study of serotonin pharmacology, it has had relatively little impact on drug design because remarkably little is known about its structure-affinity relationships.Furthermore, ketanserin also binds at 5-HT1C receptors and even less is known about the influence of its structural features on 5-HT1C receptor affinity.The present study reveals that the fluoro and carbonyl groups of the 4-fluorobenzoyl portion of ketanserin make small contributions to 5-HT2 binding and that the intact benzoylpiperidine moiety is an important feature.Ring opening of the piperidine ring reduces affinity.Although the quinazoline-2,4-dione moiety also contributes to binding, it appears to play a smaller role and can be structurally simplified with retention of 5-HT2 affinity.N-(4-Phenylbutyl)-4-(4-fluorobenzoyl)piperidine (39), for example, binds with nearly tha same affinity (Ki=5.3 nM) as ketanserin (Ki=3.5 nM).All of the compounds examined bind at 5-HT1C sites with lower affinity than ketanserin, and some of the simplified analogues bind with nearly 10 times the 5-HT2 versus 5-HT1C selectivity of ketanserin; however, none displays > 120 fold selectivity.Several of the compounds, such as the amide 32 and the urea 33 represent examples of new structural classes of 5-HT2 ligands.
