- Electrochemically Enabled Selenium Catalytic Synthesis of 2,1-Benzoxazoles fromo-Nitrophenylacetylenes
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The study reported an electrochemically mediated method for the preparation of 2,1-benzoxazoles fromo-nitrophenylacetylenes. Different from the traditional electrochemical reduction of nitro to nitroso, the nitro group directly underwent a cyclization rea
- Wang, Lin-Wei,Feng, Yu-Feng,Lin, Hong-Min,Tang, Hai-Tao,Pan, Ying-Ming
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p. 16121 - 16127
(2021/03/09)
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- Catalytic asymmetric formal [3+2] cycloaddition of isatogens with azlactones to construct indolin-3-one derivatives
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The chiral amide-guanidine-catalyzed asymmetric formal [3+2] cycloaddition of isatogens with azlactones is presented. This strategy provided a facile and feasible route to chiral indolin-3-one derivatives bearing two contiguous tetrasubstituted stereocent
- Xie, Lihua,Li, Yi,Dong, Shunxi,Feng, Xiaoming,Liu, Xiaohua
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supporting information
p. 239 - 242
(2021/01/14)
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- Oxidative Approach Enables Efficient Access to Cyclic Azobenzenes
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Azobenzenes are versatile photoswitches that have found widespread use in a variety of fields, ranging from photopharmacology to the material sciences. In addition to regular azobenzenes, the cyclic diazocines have recently emerged. Although diazocines have fascinating conformational and photophysical properties, their use has been limited by their synthetic accessibility. Herein, we present a general, high-yielding protocol that relies on the oxidative cyclization of dianilines. In combination with a modular substrate synthesis, it allows for rapid access to diversely functionalized diazocines on gram scales. Our work systematically explores substituent effects on the photoisomerization and thermal relaxation of diazocines. It will enable their incorporation into a wide variety of functional molecules, unlocking the full potential of these emerging photoswitches. The method can be applied to the synthesis of a new cyclic azobenzene with a nine-membered central ring and distinct properties.
- Maier, Martin S.,Hüll, Katharina,Reynders, Martin,Matsuura, Bryan S.,Leippe, Philipp,Ko, Tongil,Sch?ffer, Lukas,Trauner, Dirk
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supporting information
p. 17295 - 17304
(2019/11/03)
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- Compound for organic optoelectronic element, organic optoelectronic element comprising same, and display device
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The present invention relates to a compound for an organic optoelectronic element represented by Chemical Formula 1, an element comprising the same, and a display device comprising the organic optoelectronic element (details of Chemical Formula 1 are as described in the specification).
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Page/Page column 32
(2019/05/15)
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- HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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A heterocyclic compound and an organic light-emitting device including the heterocyclic compound, the heterocyclic compound being represented by Formula 1:
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-
Paragraph 0376-0377
(2018/08/29)
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- Phosphinito palladium(ii) complexes as catalysts for the synthesis of 1,3-enynes, aromatic alkynes and ynones
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An air-stable phosphinito palladium(ii) complex (Ph1-Phoxide) has been found to be an efficient catalyst in the formation of C-C bonds. The coupling of terminal alkynes formed gem-1,3-enynes as the only reaction products. Aromatic alkynes can be synthesized from the coupling of terminal alkynes and haloaromatic compounds (Sonogashira coupling). The phosphinito palladium(ii) complex also catalyses the coupling between acyl chlorides and terminal alkynes (Sonogashira coupling), furnishing ynones in excellent yields.
- Islas,Cárdenas,Gavi?o,García-Ríos,Lomas-Romero,Morales-Serna
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p. 9780 - 9789
(2017/02/15)
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- Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation
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The Rh-catalyzed hydroacylative union of aldehydes and o-alkynyl anilines leads to 2-aminophenyl enones, and onward to substituted quinolines. The mild reaction conditions employed in this chemistry result in a process that displays broad functional group
- Neuhaus, James D.,Morrow, Sarah M.,Brunavs, Michael,Willis, Michael C.
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supporting information
p. 1562 - 1565
(2016/05/02)
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- Solution processed bulk heterojunction solar cells based on A-D-A small molecules with a dihydroindoloindole (DINI) central donor and different acceptor end groups
-
Four acceptor-donor-acceptor (A-D-A) small molecules with dihydroindoloindole (DINI) as the central donor unit and different acceptor end groups such as dicyanovinylene (DCV), indenedione (IND), cyanoacrylate (CA) and rhodanine (Rho) linked through bithiophene as the π-linker, DINI-DCV, DINI-IND, DINI-CA and DINI-Rho, were designed and synthesized for the application as donor materials along with PC71BM as an acceptor for solution processed organic bulk heterojunction solar cells. The effect of acceptor end groups on the photovoltaic performance was investigated. The organic solar cells (OSCs) based on as cast DINI-IND showed the highest power conversion efficiency of 3.04%, as cast DINI-CA showed the lowest PCE of 1.63% and the other two exhibit a PCE in between them. These results showed that acceptor end groups affect the overall performance of the cells. The PCE of OSCs has been further improved up to 7.04% and 6.16% employing two-step annealing (TSA) treated DIN-IND:PC71BM (1:2) and DIN-CN:PC71BM (1:2), respectively. The enhancement in the PCE of OSCs with TSA treated active layers is attributed to the better nanophase morphology, the increase in the crystalline nature and light harvesting efficiency and more balanced charge transport and charge collection probability.
- Sim, Jangkeun,Lee, Hyejeoung,Song, Kihyoung,Biswas, Subhayan,Sharma, Abhishek,Sharma, Ganesh D.,Ko, Jaejung
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supporting information
p. 3508 - 3516
(2016/05/19)
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- ELECTROACTIVE MATERIALS
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There is disclosed a compound having Formula (I), Formula (II), Formula (III), Formula (VIII), Formula (IX), or Formula (X) The variables are described in detail in the application.
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Page/Page column 90
(2016/05/19)
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- Dicyanovinyl-substituted indolo[3,2-b] indole derivatives: Low-band-gap π-conjugated molecules for a single-component ambipolar organic field-effect transistor
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A series of low-band-gap π-conjugated molecules comprising N,N′-dihexylindolo[3,2-b]indole as an electron donor (D) and dicyanovinyl as an electron acceptor (A) with A-π-D-π-A architecture have been designed and synthesized to fabricate a single-component
- Cho, Illhun,Park, Sang Kyu,Kang, Boseok,Chung, Jong Won,Kim, Jin Hong,Yoon, Won Sik,Cho, Kilwon,Park, Soo Young
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supporting information
p. 9460 - 9468
(2016/10/25)
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- Synthesis of 2-spiropseudoindoxyls via an intramolecular nitroalkyne redox-dipolar cycloaddition cascade
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Novel spiropseudoindoxyls were synthesized in high yields via a fully regioselective Au(III)-catalyzed cycloisomerization of easily obtainable o-nitrophenylpropiolamides, followed by an intramolecular dipolar cycloaddition as key steps. This one-pot cascade reaction resulted in new tetracyclic pseudoindoxyls, which were hydrogenated toward the title compounds as single diastereomers via N-O cleavage. The mechanism of the gold catalyzed cycloisomerization was studied by DFT and suggests a reaction path without the intermediacy of gold carbenoid species in these cases.
- Marien, Niels,Brigou, Ben,Pinter, Balazs,De Proft, Frank,Verniest, Guido
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supporting information
p. 270 - 273
(2015/03/05)
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- Palladium and copper-supported on charcoal: A heterogeneous multi-task catalyst for sequential Sonogashira-Click and Click-Heck reactions
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This paper describes the development of one-pot sequential Sonogashira-Click and Click-Heck reactions by using Pd-Cu/C as a heterogeneous multi-task catalyst for the synthesis of heterocyclic structures. Details of the optimization studies and the substrate scope are discussed. These methodologies allow the preparation of functionalized triazoles in simple experimental conditions with inexpensive reagents.
- Rossy, Cybille,Majimel, Jér?me,Delapierre, Mona Tréguer,Fouquet, Eric,Felpin, Fran?ois-Xavier
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- 5,10-dihydroindolo[3,2-b]indole-based copolymers with alternating donor and acceptor moieties for organic photovoltaics
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A series of new donor-acceptor π-conjugated copolymers incorporating 5,10-dihydroindolo[3,2-b]indole (DINI) as an electron donating unit have been designed, synthesized, and explored in bulk heterojunction solar cells with diketopyrrolopyrrole and thienop
- Owczarczyk, Zbyslaw R.,Braunecker, Wade A.,Garcia, Andres,Larsen, Ross,Nardes, Alexandre M.,Kopidakis, Nikos,Ginley, David S.,Olson, Dana C.
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p. 1350 - 1360
(2013/05/08)
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- Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones
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Reductive heterocycle-heterocycle (heterocycle → heterocycle; H-H) transformations that give 4-aminoquinolines, 3-acylindoles, and quinolin-4(1H)-ones from 2-nitrophenyl substituted isoxazoles are reported. When this methodology is applied to 3,5-, 4,5-,
- Coffman, Keith C.,Palazzo, Teresa A.,Hartley, Timothy P.,Fettinger, James C.,Tantillo, Dean J.,Kurth, Mark J.
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supporting information
p. 2062 - 2065
(2013/06/05)
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- DIPEPTIDE ACETYLENE CONJUGATES AND A METHOD FOR PHOTOCLEAVAGE OF DOUBLE STRAND DNA BY DIPEPTIDE ACETYLENE CONJUGATES
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Photoreactive DNA cleaving conjugate compounds are provided comprising a DNA cleaving moiety which comprises an aryl alkyne group and a polyfunctional pH-regulated DNA-binding moiety which comprises at least one or two amino groups.
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Page/Page column 21
(2012/12/13)
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- Fine-tuning alkyne cycloadditions: Insights into photochemistry responsible for the double-strand DNA cleavage via structural perturbations in diaryl alkyne conjugates
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Hybrid molecules combining photoactivated aryl acetylenes and a dicationic lysine moiety cause the most efficient double-strand (ds) DNA cleavage known to date for a small molecule. In order to test the connection between the alkylating ability and the DN
- Yang, Wang-Yong,Marrone, Samantha A.,Minors, Nalisha,Zorio, Diego A.R.,Alabugin, Igor V.
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supporting information; experimental part
p. 813 - 823
(2011/08/10)
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- NOVEL COMPOUNDS FOR ORGANIC ELECTRONIC MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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Provided are novel compounds for organic electronic material and an organic electroluminescent device using the same. Since the compound for organic electronic material exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.
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Page/Page column 15
(2011/11/06)
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- Gold-catalyzed stereoselective synthesis of azacyclic compounds through a redox/[2 + 2 + 1] cycloaddition cascade of nitroalkyne substrates
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We report a new redox/cycloaddition cascade on readily available 1-alkynyl-2-nitrobenzenes that produces complex azacyclic compounds stereoselectively. The core structures of the resulting products are constructed through a formal [2 + 2 + 1] cycloaddition among α-carbonyl carbenoids, nitroso species, and external alkenes.
- Jadhav, Appaso Mahadev,Bhunia, Sabyasachi,Liao, Hsin-Yi,Liu, Rai-Shung
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supporting information; experimental part
p. 1769 - 1771
(2011/04/15)
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- One-pot click synthesis of 1N-alkyl-4-aryl-1,2,3-triazoles from protected arylalkynes and alkyl bromides
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1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes. Georg Thieme Verlag Stuttgart. New York.
- Ladouceur, Sebastien,Soliman, Ahmed M.,Zysman-Colman, Eli
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supporting information; experimental part
p. 3604 - 3611
(2011/12/16)
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- Copper-free Sonogashira coupling reactions catalyzed by a water-soluble Pd-salen complex under aerobic conditions
-
The water-soluble Pd-salen complex, palladium(II) N,N′-bis{[5-(triphenylphosphonium)methyl]salicylidene}-1,2-ethanediamine chloride, is a highly active catalyst for the copper-free Sonogashira coupling of aryl iodides with terminal alkynes in water under
- Bakherad, Mohammad,Keivanloo, Ali,Bahramian, Bahram,Hashemi, Mahdieh
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experimental part
p. 1557 - 1559
(2009/06/21)
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- One-Pot synthesis of indoles and aniline derivatives from nitroarenes under hydrogenation condition with supported gold nanoparticles
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One-pot sequences of hydrogenation/hydroamination to form indoles from (2-nitroaryl)alkynes and hydrogenation/reductive amination to form aniline derivatives from nitroarenes and aldehydes were catalyzed by Au nanoparticles supported on Fe2O3. Nitro group selective hydrogenations and successive reactions were efficiently catalyzed under the conditions.
- Yamane, Yoshihiro,Liu, Xiaohao,Hamasaki, Akiyuki,Ishida, Tamao,Haruta, Masatake,Yokoyama, Takushi,Tokunaga, Makoto
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supporting information; experimental part
p. 5162 - 5165
(2009/12/28)
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- A diphenylphosphinoethane-functionalized polystyrene resin-supported Pd(0) complex as an effective catalyst for copper-free Sonogashira coupling reactions under aerobic conditions
-
A polymer-supported palladium(0) diphenylphosphinoethane complex was found to be a highly active catalyst for the copper-free Sonogashira coupling reaction of aryl iodides with terminal alkynes, giving excellent yields of products (85-98%) under aerobic c
- Bakherad, Mohammad,Keivanloo, Ali,Bahramian, Bahram,Mihanparast, Samira
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experimental part
p. 6418 - 6420
(2010/02/28)
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- Diels-Alder reactions of cyclopentadienones with aryl alkynes to form biaryl compounds
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(Chemical Equation Presented) Diels-Alder reactions of cyclopentadienones, to afford substituted biaryls, were studied using an expanded substrate base. Electron-withdrawing groups on the aryl alkyne dienophile facilitated the reaction, and these substrates gave better yields than those with electron-donating substituents. Steric effects were also found to be important, and o,o′-dimethylphenylacetylene gave much poorer yield of biaryl product.
- Pearson, Anthony J.,Zhou, Yan
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scheme or table
p. 4242 - 4245
(2009/09/25)
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- Green catalysts: Solid-phase peptide carbene ligands in aqueous transition-metal catalysis
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A series of functionalized imidazolium ions containing a pyridine moiety and carboxylic acid functionality has been synthesized in solution. These compounds serve as N-heterocyclic carbene precursors and were attached to a dipeptide on solid support by means of standard peptide coupling techniques. Treatment with base generated the corresponding carbenes, which were directly complexed to palladium(II) and subsequently studied by mass spectrometry and NMR spectroscopy. The supported monocarbene catalyst 7 was successfully applied in Sonogashira and Suzuki cross-coupling reactions, and the cross-coupling products were isolated in excellent yield. Bis(carbene) catalyst 8 was successfully applied in solution in high-yielding Suzuki cross-coupling reactions. Furthermore, the catalysts proved to be stable in aqueous media, which allowed the Suzuki cross-coupling reactions to be performed in water. No loss of catalytic activity was observed when supported catalyst 7 was recycled and subjected to repetitive cycles of Suzuki cross-coupling reactions in water. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Worm-Leonhard, Kasper,Meldal, Morten
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experimental part
p. 5244 - 5253
(2009/06/07)
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- Silylated carboxamides
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Novel silylated carboxamides of the formula (I) in which R, L, R1, R2, R3, R4 and A are as defined in the description, a plurality of processes for preparing these compounds and their use for controlling unwante
- -
-
-
- SILYLATED CARBOXAMIDES
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The invention relates to novel silylated carboxamides of formula (I), wherein R, L, R1, R2, R3, R4 and A have the meaning cited in the description. The invention also relates to several methods for the production of said compounds and the use thereof in combating undesired micro-organisms.
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Page/Page column 32
(2008/06/13)
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- PYRIDYL SUBSTITUTED HETEROCYCLES USEFUL FOR TREATING OR PREVENTING HCV INFECTION
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The present invention relates to pyridyl substituted heterocycles and hydro isomers thereof and pharmaceutical compositions thereof that inhibit replication and/or proliferation of HCV virus. The present invention also relates to the use of the pyridyl he
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- Synthesis and biological activity of various derivatives of a novel class of potent, selective, and orally active prostaglandin D2 receptor antagonists. 1. Bicyclo[2.2.1]heptane derivatives
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Novel prostaglandin D2 (PGD2) receptor antagonists were synthesized as a potential new class of antiallergic agents having a bicyclo[2.2.1] heptane ring system with sulfonamide groups. Some of them exhibit extremely potent antagonism of the PGD2 receptor in radioligand binding and cAMP formation assays with IC50 values below 50 nM and much less antagonism of TXA2 and PGI2 receptors. These potent PGD2 receptor antagonists, when given orally, dramatically suppress various allergic inflammatory responses such as increased vascular permeability in allergic rhinitis, conjunctivitis, and asthma models. The excellent pharmacological profiles of PGD2 receptor antagonists, originally synthesized in our laboratories, are of potentially great clinical significance. This study also provides experimental evidence suggesting that PGD2 plays an important role in the pathogenesis of allergic diseases.
- Mitsumori, Susumu,Honma, Tsunetoshi,Tsuri, Tatsuo,Hiramatsu, Yoshiharu,Okada, Toshihiko,Hashizume, Hiroshi,Inagaki, Masanao,Arimura, Akinori,Yasui, Kiyoshi,Asanuma, Fujio,Kishino, Junji,Ohtani, Mitsuaki
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p. 2436 - 2445
(2007/10/03)
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- Palladium-catalyzed carbon-carbon coupling reactions using aryl Grignards
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Coupling reactions using Pd(PPh3)4 were investigated with a number of electron donating and electron withdrawing substituents. High yields were obtained with both types of substituents. In competitive reactions the electron-withdrawi
- Gottardo, Christine,Aguirre, Andrea
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p. 7091 - 7094
(2007/10/03)
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- An Unusual Example of a 6-Endo-Dig Addition to an Unactivated Carbon-Carbon Triple Bond
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Methyl 2-ethynyl>benzoate was prepared as an intermediate for subsequent conversion to an α-diazo ketone.Under the basic conditions used to hydrolyze the methyl ester, the neighboring hydroxyl functionality underwent reaction with the unactivated acetylenic group, producing a benzopyranyl-substituted α-diazoacetophenone.Treatment of this diazocarbonyl compound with a catalytic quantity of rhodium(II) mandelate afforded a novel dibenzocyclononenone derivative.The reaction proceeds via an initially formed oxonium ylide which rearranges further by means of a 1,2-alkyl shift.A prime factor in determining the direction of internal cyclization to the triple bond is the presence of the carbomethoxy group in the ortho position of the β-phenyl ring.Thus, in contrast with related systems which exhibit a clear preference for 5-exo-dig cyclization at the acetylenic center, the 6-endo-dig addition is the preferred pathway for the o-formyl- and o-carbomethoxy-substituted alkynyl alcohols.Careful monitoring of the reaction actually showed that the reaction proceeds by initial formation of the 5-exo-dig product followed by a novel rearrangement to the 6-endo product.
- Padwa, Albert,Krumpe, Keith E.,Weingarten, M. David
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p. 5595 - 5603
(2007/10/03)
-
- Prototypes for the polaronic ferromagnet. Synthesis and characterization of high-spin organic polymers
-
Preparation and characterization of several new polymers (1-7) that are considered one-dimensional prototypes for the polaronic ferromagnet are reported. Synthesis involved either Wittig or Suzuki coupling to produce polymers with extended π systems. Oxid
- Murray, Michael M.,Kaszynski, Piotr,Kaisaki, David A.,Chang, Wonghil,Dougherty, Dennis A.
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p. 8152 - 8161
(2007/10/02)
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- Condensed Heteroaromatic Ring Systems. XIII. One-Step Synthesis of 2-Substituted 1-Methylsulfonylindoles from N-(2-Halophenyl)methanesulfonamides
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The reaction of N-(2-bromophenyl)- and N-(2-iodophenyl)methanesulfonamide with terminal acetylenes in the presence of dichlorobis(triphenylphosphine)palladium yielded 1-methylsulfonylindoles having carbon-functional groups at the 2-position, such as hydroxymethyl, 2-hydroxyethyl, diethoxymethyl, 2-ethoxycarbonylethyl, etc., in one step.Keywords - palladium-catalyzed reaction; dichlorobis(triphenylphosphine)palladium; N-(2-halophenyl)methanesulfonamide; acetylene; 2-substituted 1-methylsulfonylindole.
- Sakamoto, Takao,Kondo, Yoshinori,Iwashita, Shigeki,Nagano, Tatsuo,Yamanaka, Hiroshi
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p. 1305 - 1308
(2007/10/02)
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- Condensed Heteroaromatic Ring Systems. VI. Synthesis of Indoles and Pyrrolopyridines from o-Nitroarylacetylenes
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Catalytic hydrogenation of o-nitrophenylacetaldehyde diethyl acetal over palladium-carbon, followed by intramolecular cyclization of the resulting o-aminophenylacetaldehyde diethyl acetal with hydrochloric acid, gave indole.Similarly, 4-methylindole, ethyl 5-indolecarboxylate, and various pyrrolopyridines were synthesized from the corresponding o-nitroarylacetaldehyde derivatives.The preparation of the desired o-nitroarylacetaldehydes was accomplished by the condensation of o-halonitroaromatics with trimethylsilylacetylene in the presence of dichloro-bis(triphenylphosphine)palladium as a catalyst, followed by ethanolysis of the resulting o-(trimethylsilylethenyl)nitroaromatics.Keywords - o-halonitroaromatic; o-cyanohaloaromatic; trimethylsilylacetylene; palladium-catalyzed reaction; cyclization; indole; pyrrolopyridine
- Sakamoto, Takao,Kondo, Yoshinori,Yamanaka, Hiroshi
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p. 2362 - 2368
(2007/10/02)
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