2150-40-5Relevant academic research and scientific papers
An efficient one-pot synthesis of phenol derivatives by ring opening and rearrangement of diels-alder cycloadducts of substituted furans using heterogeneous catalysis and microwave irradiation
Moreno, Andrés,Gómez, María Victoria,Vázquez, Ester,De La Hoz, Antonio,Díaz-Ortiz, Angel,Prieto, Pilar,Mayoral, José Antonio,Pires, Elisabet
, p. 1259 - 1263 (2004)
The use of silica-supported Lewis acids as catalysts under microwave irradiation promotes regiospecific opening of the 7-oxa bridge of Diels-Alder cycloadducts of furan derivatives and produces polysubstituted phenols in a single step. This rapid and effi
Photoracemization of Blestriarene C and Its Analogs
Natori, Koichi,Iwayama, Taizo,Yamabe, Osamu,Kitamoto, Yuichi,Ikeda, Hiroshi,Sakamoto, Kenkichi,Hattori, Tetsutaro,Miyano, Sotaro
, p. 479 - 486 (2015)
Two analogs of blestriarene C (4,4'-dimethoxy-1,1'-biphenanthrene-2,2',7,7'-tetraol) bearing no 7,7'-dihydroxy (3) and 4,4'-dimethoxy groups 4 were prepared. Unlike blestriarene C (1), compounds 3 and 4, as well as 1,1'-biphenanthrene-2,2'-diol (5), do not racemize under fluorescent lamp illumination. Cyclic voltammetry analysis reveals that compound 1 has a lower half-wave potential (E1/2) than compounds 3, 4, 5, suggesting that a redox cycle is involved in the racemization. Compound 1 racemizes by absorbing UV light corresponding to the 1Lb band. During the reaction, no side products are observed. The racemization is significantly inhibited under nitrogen. Based on these observations, we propose a feasible mechanism for the easy racemization of compound 1, which is mediated by a cation radical generated in situ by a reversible photo-induced oxygen oxidation. Chirality 27:479-486, 2015.
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.
Conversion of alcohols to alkyl esters and carboxylic acids using heterogeneous palladium-based catalysts
-
Sheet 3, (2017/04/28)
Disclosed are methods for synthesizing an ester or a carboxylic acid from an organic alcohol. To form the ester one reacts, in the presence of oxygen gas, the alcohol with methanol or ethanol. This reaction occurs in the presence of a catalyst comprising palladium and a co-catalyst comprising bismuth, tellurium, lead, cerium, titanium, zinc and/or niobium (most preferably at least bismuth and tellurium). Alternatively that catalyst can be used to generate an acid from that alcohol, when water is also added to the reaction mix.
Hydrogen-Bonding-Induced Fluorescence: Water-Soluble and Polarity-Independent Solvatochromic Fluorophores
Okada, Yohei,Sugai, Masae,Chiba, Kazuhiro
, p. 10922 - 10929 (2016/11/29)
Fluorophores with emission wavelengths that shift depending on their hydrogen-bonding microenvironment in water would be fascinating tools for the study of biological events. Herein we describe the design and synthesis of a series of water-soluble solvatochromic fluorophores, 2,5-bis(oligoethylene glycol)oxybenzaldehydes (8-11) and 2,5-bis(oligoethylene glycol)oxy-1,4-dibenzaldehydes (14-17), based on a push-pull strategy. Unlike typical examples in this class of fluorophores, the fluorescence properties of these compounds are independent of solvent polarity and become fluorescent upon intermolecular hydrogen-bonding, exhibiting high quantum yields (up to φ = 0.55) and large Stokes shifts (up to 134 nm). Furthermore, their emission wavelengths change depending on their hydrogen-bonding environment. The described fluorophores provide a starting point for unprecedented applications in the fields of chemical biology and medicinal chemistry.
Design and synthesis of diaziridinyl quinone thiadiazole hybrids via nitrile sulfide cycloaddition reaction as a key step
Aitha, Anjaiah,Yennam, Satyanarayana,Behera, Manoranjan,Anireddy, Jaya Shree
supporting information, p. 1507 - 1510 (2016/03/12)
A series of novel diaziridinyl quinone thiadiazole hybrids (9a-9j) were synthesized starting from 2-hydroxy-5-methoxybenzoic acid 1 in a 7 step synthetic sequence. The key step in the scheme involves the nitrile sulfide cycloaddition reaction of oxathiazo
Isatin based Schiff bases as inhibitors of α-glucosidase: Synthesis, characterization, in vitro evaluation and molecular docking studies
Rahim, Fazal,Malik, Fazal,Ullah, Hayat,Wadood, Abdul,Khan, Fahad,Javid, Muhammad Tariq,Taha, Muhammad,Rehman, Wajid,Ur Rehman, Ashfaq,Khan, Khalid Mohammed
, p. 42 - 48 (2015/05/13)
Isatin base Schiff bases (1-20) were synthesized, characterized by 1H NMR and EI/MS and evaluated for α-glucosidase inhibitory potential. Out of these twenty (20) compounds only six analogs showed potent α-glucosidase inhibitory potential with IC50 value ranging in between 2.2 ± 0.25 and 83.5 ± 1.0 μM when compared with the standard acarbose (IC50 = 840 ± 1.73 μM). Among the series compound 2 having IC50 value (18.3 ± 0.56 μM), 9 (83.5 ± 1.0 μM), 11 (3.3 ± 0.25 μM), 12 (2.2 ± 0.25 μM), 14 (11.8 ± 0.15 μM), and 20 (3.0 ± 0.15 μM) showed excellent inhibitory potential many fold better than the standard acarbose. The binding interactions of these active analogs were confirmed through molecular docking.
New pyrazole derivatives as CRAC channel modulators
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Paragraph 0093; 0096, (2015/03/28)
The present invention relates to compounds of formula (I) which are inhibitors of CRAC channel activity. This invention also relates to pharmaceutical compositions containing them, process for their preparation and their use in therapy.
NMR methodology for complex mixture 'separation'
Bell, Nicholle G. A.,Murray, Lorna,Graham, Margaret C.,Uhrin, Dusan
supporting information, p. 1694 - 1697 (2014/02/14)
Mixture 'separation' by NMR is demonstrated through the development of a pseudo 4D NMR experiment, 3D IPAP INEPT-INADEQUATE-HSQC, designed for the structural elucidation of 13C tagged compounds.
Aerobic oxidation of diverse primary alcohols to methyl esters with a readily accessible heterogeneous Pd/Bi/Te catalyst
Powell, Adam B.,Stahl, Shannon S.
supporting information, p. 5072 - 5075 (2013/10/22)
Efficient aerobic oxidative methyl esterification of primary alcohols has been achieved with a heterogeneous catalyst consisting of 1 mol % Pd/charcoal (5 wt %) in combination with bismuth(III) nitrate and tellurium metal. The Bi and Te additives significantly increase the reaction rate, selectivity, and overall product yields. This readily accessible catalyst system exhibits a broad substrate scope and is effective with both activated (benzylic) and unactivated (aliphatic) alcohols bearing diverse functional groups.
