108791-66-8Relevant articles and documents
Novel Catechol Derivatives of Arylimidamides as Antileishmanial Agents
Rezaei, Foroogh,Saghaie, Lotfollah,Sabet, Razieh,Fassihi, Afshin,Hatam, Gholamreza
, (2018)
Two novel bis-arylimidamide derivatives with terminal catechol moieties (9a and 10a) and two parent compounds with terminal phenyl groups (DB613 and DB884) were synthesized as dihydrobromide salts (9b and 10b). The designed compounds were hybrid molecules
Flexible and highly fluorescent aromatic polyimide: design, synthesis, properties, and mechanism
Zhou, Zhuxin,Zhang, Yi,Liu, Siwei,Chi, Zhenguo,Chen, Xudong,Xu, Jiarui
, p. 10509 - 10517 (2016)
To develop high-performance flexible fluorescent aromatic polyimides and to have a deeper insight into the fluorescence mechanism, two diamine monomers PyDA and TzDA with similar chemical structures but totally different electronic effects, were designed and synthesized. PyDA bears an electron-donor pyrrole group while TzDA bears an electron-acceptor 1,2,4-triazole group. The resulting aromatic polyimide TzODPI containing the triazole group showed bright green photoluminescence with a high quantum yield of up to 61% in solution and 13% in the film state. However, fluorescence was totally quenched in the pyrrole-containing polyimide PyODPI. The completely different phenomena were systematically elucidated with the aid of molecular simulations. Theoretical calculations for the molecular orbital distribution, oscillator strength, and the electron transition process between the ground state and excited state of model molecules were applied to clarify the fluorescence mechanism. Highly fluorescent aromatic polyimides can be obtained by appropriate control of the intra-molecular charge-transfer effects between the diamine and dianhydride moieties, and this demonstrates a simple strategy to develop wholly aromatic polyimides with high fluorescence for potential applications in the field of flexible displays.
Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles
Schirmacher, Robert H.E.,R?sch, Daniel,Thomas, Franziska
, (2021/02/20)
An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles.
Catalytic Enantioselective Total Synthesis of (+)-Lycoperdic Acid
Kortet, Sami,Claraz, Aurélie,Pihko, Petri M.
supporting information, p. 3010 - 3013 (2020/04/10)
A concise enantio- and stereocontrolled synthesis of (+)-lycoperdic acid is presented. The stereochemical control is based on iminium-catalyzed Mukaiyama-Michael reaction and enamine-catalyzed organocatalytic α-chlorination steps. The amino group was introduced by azide displacement, affording the final stereochemistry of (+)-lycoperdic acid. Penultimate hydrogenation and hydrolysis afforded pure (+)-lycoperdic acid in seven steps from a known silyloxyfuran.
Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes
Zhu, Xiaolin,Lin, Yixiong,Sun, Yue,Beard, Matthew C.,Yan, Yong
supporting information, p. 733 - 738 (2019/01/23)
Cost-effective and efficient photocatalysis are highly desirable in chemical synthesis. Here we demonstrate that readily prepared suspensions of APbBr3 (A = Cs or methylammonium (MA)) type perovskite colloids (ca. 2-100 nm) can selectively photocatalyze carbon-carbon bond formation reactions, i.e., α-alkylations. Specifically, we demonstrate α-alkylation of aldehydes with a turnover number (TON) of over 52,000 under visible light illumination. Hybrid organic/inorganic perovskites are revolutionizing photovoltaic research and are now impacting other research fields, but their exploration in organic synthesis is rare. Our low-cost, easy-to-process, highly efficient and bandedge-tunable perovskite photocatalyst is expected to bring new insights in chemical synthesis.
Synthesis of 1,4-Diketones via Titanium-Mediated Reductive Homocoupling of α-Haloketones
Le, Nathan N.,Rodriguez, Aimee M.,Alleyn, James R.,Gesinski, Michael R.
, p. 2195 - 2198 (2018/09/29)
1,4-Diketones have been synthesized via a reductive homocoupling of α-haloketones. Addition of a Grignard reagent to titanium(IV) isopropoxide affords a low-valent titanium(III) intermediate that is believed to mediate a radical dimerization reaction. The
Nonvolatile electrical switching behavior and mechanism of functional polyimides bearing a pyrrole unit: Influence of different side groups
Zhou, Zhuxin,Qu, Lunjun,Yang, Tingting,Wen, Jinglan,Zhang, Yi,Chi, Zhenguo,Liu, Siwei,Chen, Xudong,Xu, Jiarui
, p. 52798 - 52809 (2016/06/14)
To better understand the structure-property relationships and the mechanisms of the electronic switching behavior of functional polyimides, a new series of diamines containing a pyrrole core with different side groups were designed and synthesized. Three novel, thermally stable and aromatic polyimides (Py6FPIs) containing the as-designed diamines were prepared. They were fabricated into memory devices sandwiched between an Al top electrode and an indium-tin oxide (ITO) bottom electrode by spin-coating. The polyimides exhibited high thermal stability with glass transition temperatures (Tg) around 300 °C as determined by DMA. The memory devices were found to show nonvolatile bistable write-once-read-many (WORM) memory characteristics with diverse switching threshold voltages and ON/OFF ratios, depending on the electron affinity of the pendent groups. The low-conductivity state and the high-conductivity state could be sustained under a constant bias or a refreshing voltage pulse of 1.0 V. The switching mechanism and the memory effects were finely demonstrated with the aid of molecular simulations and electronic absorption spectra of these Py6FPIs.
A simple method for the synthesis of furfuryl ketones and furylacetic acid derivatives
Chalikidi, Petrakis N.,Nevolina, Tatyana A.,Uchuskin, Maxim G.,Abaev, Vladimir T.,Butin, Alexander V.
, p. 621 - 629 (2015/10/12)
A simple preparative method has been developed for the synthesis of aryl(furfuryl) ketones, amides, and furylacetic acid esters, based on radical alkylation of furan derivatives at the α-position with O-ethyl(phenacyl)xanthogenates and phenacyl iodides in the presence of Fenton's reagent (H2O2/FeSO4·7H2O) in DMSO. The range of applicability and mechanisms for the formation of major and side products have been considered.
ANTI-VIRAL COMPOUND
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Paragraph 0024, (2015/11/27)
The present invention features crystalline forms of Compound I.
Breaking bonds with electrons: Stepwise and concerted reductive cleavage of C-S, C-Se and Se-CN bonds in phenacylthiocyanates and phenacylselenocyanates
Bouchet, Lydia M.,Peory, Alicia B.,Robert, Marc,Argüello, Juan E.
, p. 11753 - 11760 (2015/02/19)
The mechanistic aspects of the electrochemical reduction of phenacylthio- and selenocyanates have been studied. With phenacylthiocyanates (1), a change in the reductive cleavage mechanism is observed as a function of the substituent on the phenyl ring. While a stepwise mechanism involving the intermediacy of a radical anion is followed for substrates bearing a strong electron withdrawing group, such as cyano and nitro substituent (1d, 1e), and a concerted mechanism is favoured for compounds bearing an electron-donating or no substituent on the phenyl ring (1a-c). A regioselective bond cleavage leads to the fragmentation of the CH2-S bond with all compounds 1a-e, further yielding the corresponding 1,4-diketone (3) as products. Contrastingly, with phenacylselenocyanates (2), two different reductive cleavages occur involving the breaking of both the CH2-Se and Se-CN bonds. Several products are obtained, all coming from nucleophilic attack at the α (phenacyl) carbon or the selenium atom.