54897-52-8Relevant academic research and scientific papers
Detection and identification of loline and its analogues in horse urine
Takeda,Suzuki,Kamei,Nakata
, p. 964 - 968 (1991)
Several kinds of loline-type alkaloids, norloline, loline, N-acetylnorloline, N-acetylloline, N-formylnorloline, N-formylloline and N-methylloline were detected in the urine of race-horses. Furthermore, a new compound of the alkaloids, N-senecioylnorlolin
CHROMAN-SUBSTITUTED, TETRAHYDROQUINOLINE-SUBSTITUTED AND THIOCHROMAN-SUBSTITUTED HETEROAROTINOIDS AS ANTI-CANCER AGENTS
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Paragraph 0221-0222; 0241; 0296, (2020/03/09)
Chemical compounds that inhibit cancer cell growth are provided. The compounds are heteroarotinoids and derivatives thereof with oxygen, nitrogen or sulfur in chroman systems, tetrahydroquinoline systems, and tetrahydrothiochroman systems.
Activity of oxygen-versus sulfur-containing analogs of the Flex-Het anticancer agent SHetA2
Watts, Field M.,Pouland, Tim,Bunce, Richard A.,Berlin, K. Darrell,Benbrook, Doris M.,Mashayekhi, Maryam,Bhandari, Dipendra,Zhou, Donghua
, p. 720 - 732 (2018/09/29)
Five series of chromans with urea and thiourea linkers connecting a chroman unit (ring A) and a 4-substituted benzene unit (ring B) have been prepared and evaluated relative to SHetA2 (NSC 721689) for activity against the human A2780 ovarian cancer cell l
Bismuth(III) triflate catalyzed tandem esterification–Fries–oxa-Michael route to 4-chromanones
Meraz, Kevin,Gnanasekaran, Krishna Kumar,Thing, Rup,Bunce, Richard A.
supporting information, p. 5057 - 5061 (2016/11/02)
An efficient tandem reaction approach is described to prepare 4-chromanones from electron-rich phenols and 3,3-dimethylacrylic acid or trans-crotonic acid in boiling toluene using 20?mol?% bismuth(III) triflate as the catalyst. The reaction is also successful from the corresponding aryl esters of each of these acids under the same conditions. The procedure is convenient to perform, and 25–90% yields of products are realized following chromatography. A range of substrates is included (14 substrates for each acid) to help define the scope of the process. Additional experiments are reported, which confirm that the sequence of events involves (1) esterification, (2) Fries rearrangement and (3) oxa-Michael ring closure.
Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones
Iguchi, Daniela,Erra-Balsells, Rosa,Bonesi, Sergio M.
, p. 4653 - 4656 (2015/02/19)
A facile photochemical preparation of 5-, 6-, and 7-substituted chroman-4-ones from aryl 3-methyl-2-butenoate esters is described. The two-phase base-catalyzed method relies upon two consecutive processes in one-pot reaction through a photo-Fries rearrangement and a based-catalyzed intramolecular oxa-Michael addition to afford the desired products.
One-pot ester synthesis from allyl and benzyl halides and alcohols by palladium-catalyzed carbonylation
Tommasi, Sara,Perrone, Serena,Rosato, Francesca,Salomone, Antonio,Troisi, Luiginio
experimental part, p. 423 - 430 (2012/03/11)
A mild and efficient one-pot synthesis of esters based on the Pd-catalyzed alkoxy- and aryloxycarbonylation of allylic and benzylic halides is described. The methodology has been applied to primary, secondary, and tertiary alcohols as well as to phenol derivatives. The O-protection of some biologically relevant molecules is also reported. Georg Thieme Verlag Stuttgart New York.
HETEROCYCLIC COMPOUNDS USEFUL AS ANABOLIC AGENTS FOR LIVESTOCK ANIMALS
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Page/Page column 98-99, (2008/06/13)
Compounds of formula (I) and pharmaceutically acceptable salts thereof are agonists at the beta-2 adrenoceptor. They are useful as feed additives for livestock animals.
Investigation of the Rh-catalyzed asymmetric reductive aldol reaction. Expanded scope based on reaction analysis
Russell, Albert E.,Fuller, Nathan O.,Taylor, Steven J.,Aurriset, Pauline,Morken, James P.
, p. 2309 - 2312 (2007/10/03)
(Equation Presented) A series of experiments are described that suggest that the Rh-catalyzed reductive aldol reaction proceeds by addition of a Rh(I) hydride, generated in situ, to the reacting acrylate followed by a stereochemistry-controlling aldol add
Reactivity of α,α′-dichloroketones towards anions electrogenerated at carbonium and oxygen atoms. Electrochemically-induced Favorskii rearrangement. Part 2
Chiarotto, Isabella,Feroci, Marta,Giomini, Claudio,Inesi, Achille
, p. 167 - 175 (2007/10/03)
Electrolyses of solutions containing α,α′-dichloroketones 1a or 2a were carried out, on a mercury pool or glassy carbon cathode, at a potential sufficiently negative to allow two-electron cleavage of the C-Cl bond. The effects of the presence of carboxylic acids 3a,b, phenols 4a-f, or carbon acid 5 in the solutions were evaluated. Depending on the type of acidic substrate, it was possible to isolate from the cathodic solutions the Favorskii-rearrangement products 9m, 10m, 11 and 12, as well as dechlorinated ketones 1b and 2b and the addition products 7m and 8m. The conditions under which it was possible, by electrochemical means, to induce the Favorskii rearrangement between dichloroketones 1a and 2a and the acidic substrates are discussed. Evidence was gained by voltammetric analysis that the rates of formation of the Favorskii adducts 9a-f depend on the structures of the corresponding phenols 4a-f. By employing electrogenerated bases, it was possible to obtain α,β-unsaturated ketones at potentials less negative than required for the direct reduction of 1a and 2a. Elsevier.
ON THE REACTION OF SUBSTITUTED PHENOLS AND 3-METHYLBUT-2-ENOIC ACID. A COMPARATIVE STUDY
Seboek, Peter,Jekoe, Jozsef,Timar, Tibor,Jaszberenyi, Joseph Cs.
, p. 2099 - 2114 (2007/10/02)
A systematic and comparative study of the reaction of a series of substituted phenols and 3-methylbut-2-enoic acid in zinc chloride/phosphorus oxychloride and aluminum chloride/phosphorus oxychloride reveals that the formation of phenolic esters and 2,2-dimethyl-4-chromanones is strongly influenced by the substituents, their popsition on the aromatic ring of the starting phenols.Based on our study, a mixed Friedel-Crafts and Fries rearrangement mechanism is in operation in these reactions.
