2905-82-0Relevant articles and documents
Expeditious and practical synthesis of tertiary alcohols from esters enabled by highly polarized organometallic compounds under aerobic conditions in Deep Eutectic Solvents or bulk water
Quivelli, Andrea F.,D'Addato, Giovanna,Vitale, Paola,García-álvarez, Joaquín,Perna, Filippo M.,Capriati, Vito
, (2021/01/18)
An efficient protocol was developed for the synthesis of tertiary alcohols via nucleophilic addition of organometallic compounds of s-block elements (Grignard and organolithium reagents) to esters performed in the biodegradable choline chloride/urea eutectic mixture or in water. This approach displays a broad substrate scope, with the addition reaction proceeding quickly (20 s reaction time) and cleanly, at ambient temperature and under air, straightforwardly furnishing the expected tertiary alcohols in yields of up to 98%. The practicability of the method is exemplified by the sustainable synthesis of some representative S-trityl-L-cysteine derivatives, which are a potent class of Eg5 inhibitors, also via telescoped one-pot processes.
Rhodium(III)-Catalyzed Oxidative Intramolecular 1,1-Oxyamination of Alkenes with Protected Amino Acids to Produce Oxazoloisoindole-2,5-diones
Takahashi, Hiroto,Nagashima, Yuki,Tanaka, Ken
supporting information, p. 1891 - 1895 (2021/04/05)
It has been established that an electron-deficient bis(ethoxycarbonyl)-substituted cyclopentadienyl (CpE) rhodium(III) complex catalyzes the oxidative intramolecular 1,1-oxyamination of alkenes with N-benzoyl amino acids to produce oxazoloisoindole-2,5-diones. Experimental and theoretical mechanistic studies revealed that this oxidative 1,1-oxyamination proceeds via not the aza-Wacker reaction but the formation of a rhoda(III)oxazolidine initiated by the carboxylic acid-directed N?H bond cleavage.
Evaluation of novel N′-(3-hydroxybenzoyl)-2-oxo-2H-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors
Jesumoroti, Omobolanle J.,Faridoon,Mnkandhla, Dumisani,Isaacs, Michelle,Hoppe, Heinrich C.,Klein, Rosalyn
, p. 80 - 88 (2019/01/30)
In an attempt to identify potential new agents that are active against HIV-1 IN, a series of novel coumarin-3-carbohydrazide derivatives were designed and synthesised. The toxicity profiles of these compounds showed that they were non-toxic to human cells and they exhibited promising anti-HIV-1 IN activities with IC50 values in nM range. Also, an accompanying molecular modeling study showed that the compounds bind to the active pocket of the enzyme.
Microwave-Assisted Synthesis of Benzofuran-3(2H)-ones
Hu, Xiaojing,Lai, Huimin,Zhao, Fangfei,Hu, Shuyu,Sun, Qianqian,Fang, Lizhen
, p. 745 - 750 (2019/10/14)
A new method for the synthesis of benzofuran-3(2H)-ones under microwave conditions was developed. The reaction conditions were screened, and the scope of benzoate substrates was investigated. The results showed that our method could provide rapid access to these important dihydrobenzofuranones in 43% to 58% yields.
Gold promoted arylative cyclization of alkynoic acids with arenediazonium salts
Carrillo-Arcos, Ulises A.,Porcel, Susana
supporting information, p. 1837 - 1842 (2018/03/23)
Alkynoic acids derived from salicylic acid and analogues undergo arylative cyclization with arenediazonium salts promoted by gold in the absence of external ligands. The reaction is thermally induced and proceeds even in the absence of light. A difference in regioselectivity has been found compared with that observed in the cycloisomerization process of the same type of compounds.
Vitamin Catalysis: Direct, Photocatalytic Synthesis of Benzocoumarins via (-)-Riboflavin-Mediated Electron Transfer
Morack, Tobias,Metternich, Jan B.,Gilmour, Ryan
supporting information, p. 1316 - 1319 (2018/03/09)
An operationally simple protocol is disclosed to facilitate entry to benzo-3,4-coumarins directly from biaryl carboxylic acids without the need for substrate prefunctionalization. Complementary to classic lactonization strategies, this disconnection relies on the oxidation competence of photoactivated (-)-riboflavin (vitamin B2) to generate the heterocyclic core via photoinduced single electron transfer. Collectively, the inexpensive nature of the catalyst, ease of execution, and absence of external metal additives are a convincing endorsement for the incorporation of simple vitamins in contemporary catalysis.
11C- and 18F-Labeled Radioligands for P-Glycoprotein Imaging by Positron Emission Tomography
Cantore, Mariangela,Benadiba, Marcel,Elsinga, Philip H.,Kwizera, Chantal,Dierckx, Rudi A. J. O.,Colabufo, Nicola Antonio,Luurtsema, Gert
, p. 108 - 118 (2016/01/15)
P-Glycoprotein (P-gp) is an efflux transporter widely expressed at the human blood-brain barrier. It is involved in xenobiotics efflux and in onset and progression of neurodegenerative disorders. For these reasons, there is great interest in the assessmen
Oxidative cyclization of alkenoic acids promoted by AgOAc
Carrillo-Arcos, Ulises A.,Rojas-Ocampo, Jonathan,Porcel, Susana
supporting information, p. 479 - 483 (2016/01/09)
Alkenoic acids derived from salicylic acid and analogues undergo an unexpected oxidative cyclization process triggered by AgOAc leading to 4H-benzo[d][1,3]dioxin-4-ones. The process is affected by the substitution on the aryl and the allyl units.
Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide
Camelio, Andrew M.,Liang, Yong,Eliasen, Anders M.,Johnson, Trevor C.,Yuan, Changxia,Schuppe, Alex W.,Houk,Siegel, Dionicio
, p. 8084 - 8095 (2015/09/01)
The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.
CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF
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Page/Page column 10, (2014/10/15)
The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.