- New Indolo[3,2-b]indole based small organic molecules for Organic Thin Film Transistors (OTFTs): A combined experimental and DFT Study
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Synthesis of new indolo[3,2-b]indoles (5a- 5j) in presence of Ag-doped ZnO and (Diacetoxyiodo) benzene system under visible-light have been reported. All the new fused linear heterocyclic indolo[3,2-b]indole systems (5a- 5j) thoroughly characterized by spectroscopic methods like mass, UV-visible, NMR and C, H, N elemental analysis. Further, their photophysical properties were carried out by combined experimental and theoretical studies. Thermogravimetric studies are carried out to confirm the thermal stability of molecules. The frontier molecular orbitals of molecules are characterized with the help of cyclic voltammetry. Additionally, the compounds of series 5 were used for the fabrication of organic thin-film transistors, which indicated the hole mobilities in the range of 0.11 – 0.85 cm2/Vs and with on/off ratio 105 on ODTS-SiO2 substrate at 50 °C and are also supported by DFT studies.
- Puli, Venkat Swamy,Subburu, Mahesh,Bhongiri, Yadagiri,Tripathi, Anuj,Prasad,Chatterjee, Anindita,Pola, Someshwar,Chetti, Prabhakar
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- Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles
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We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindolesviaPd-catalyzed bis-arylative cyclization of variouso-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.
- Wang, Jiwei,Wang, Gendi,Cheng, Xiang,Liu, Ye,Zhang, Jun
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p. 1329 - 1333
(2021/02/26)
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- Copper-Catalyzed Trifluoromethylation/Cyclization of Alkynes for Synthesis of Dioxodibenzothiazepines
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A facile and efficient approach for the synthesis of the CF3-containing dioxodibenzothiazepines has been developed via copper-catalyzed trifluoromethylation/cyclization of alkynes utilizing a radical relay strategy. This method has demonstrated low cataly
- Zhang, Zi-Qi,Xu, Yi-Hao,Dai, Jing-Cheng,Li, Yan,Sheng, Jie,Wang, Xi-Sheng
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p. 2194 - 2198
(2021/04/05)
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- NOVEL LXR MODULATORS WITH BICYCLIC CORE MOIETY
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The present invention relates to bicyclic compounds (e.g. indoles) containing a sulfonyl moiety, which bind to the liver X receptor (LXRα and/or LΧΚβ) and act preferably as inverse agonists of LXR.
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Page/Page column 47
(2020/01/24)
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- Copper-Catalyzed Tandem Cross-Coupling/[2 + 2] Cycloaddition of 1,6-Allenynes with Diazo Compounds to 3-Azabicyclo[5.2.0] Ring Systems
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An unprecedented copper-catalyzed tandem cross-coupling/[2 + 2] cycloaddition of 1,6-allenynes with diazo compounds was reported, chemo- and regioselectively providing 3-azabicyclo[5.2.0] frameworks in moderate to excellent yields under mild reaction conditions. Moreover, the products readily convert to highly functionalized quinolines via oxidative radical rearrangement.
- He, Min,Chen, Nuan,Zhou, Ting,Li, Qing,Li, Hongguang,Lang, Ming,Wang, Jian,Peng, Shiyong
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p. 9559 - 9563
(2019/11/21)
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- Enantioselective A3-Coupling Reaction Employing Chiral CuI-i PrpyboxdiPh/ N-Boc-(l)-Proline Complex under Cooperative Catalysis: Application in the Synthesis of (Indol-2-yl)methanamines
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An efficient route to enantioenriched propargylamines via a three-component alkynylation reaction using cooperative catalysis with a CuI-iPrpyboxdiPh complex and N-Boc-(l)-proline has been accomplished. A variety of functionalized amines, aldehydes, and 2-ethynyl anilines were reacted smoothly at ambient temperature to furnish a wide range of propargylamines in high yields (up to 94%) and excellent enantioselectivities (up to 98% ee). Synthetic utility of the methodology has been demonstrated by transforming the products into various synthetically useful intermediates. Finally, propargylamines were transformed into biologically important (indol-2-yl)methanamines over two steps in good yields (up to 88%) with an excellent level of enantioselectivities (up to 95%).
- Dhanasekaran, Sivasankaran,Kannaujiya, Vinod. K.,Biswas, Rayhan G.,Singh, Vinod K.
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p. 3275 - 3292
(2019/03/11)
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- Intramolecular Hydroamination of Selenoalkynes to 2-Selenylindoles in the Absence of Catalyst
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In this work, a series of 2-chalcogenylindoles was synthesized by an efficient methodology, starting from chalcogenoalkynes, including a previously unreported tellurium indole derivative. For the first time, these 2-substituted chalcogenylindoles were obtained in the absence of metal catalyst or base, under thermal conditions only. In addition, the results described herein represent a methodology with inverse regioselectivity for the chalcogen functionalization of indoles.
- Coelho, Felipe L.,Gil, Eduarda S.,Gon?alves, Paulo F. B.,Campo, Leandra F.,Schneider, Paulo H.
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supporting information
p. 8157 - 8162
(2019/05/29)
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- Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines
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A room temperature and silver-free protocol for the formation of quinolines from 2-ethynylanilines through a dimerization event was achieved using a dinuclear gold catalyst, Au2(BIPHEP)(NTf2)2. The reaction is inherently modular, allowing for the incorporation of peripheral substituents at any site of the quinoline product. The reaction is readily applied to other heterocyles also as exemplified by the preparation of naphthyridines. Competition reactions to determine the reactivity of dissimilar alkynes demonstrated that the product ratio of dimerization vs intermolecular addition is rather dependent on the electronic nature of aryl substituent on the alkynes. However, control experiments with substrates possessing internal alkynes resulted in cycloisomerization instead of expected dimerization, which is indicative of possible steric influence of the alkyne terminus in the reaction outcome.
- Praveen, Chandrasekar,Perumal
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p. 855 - 864
(2016/03/15)
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- ALKYNE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
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Provided are compounds of formula (Ia) and pharmaceutically acceptable salts thereof, wherein A, B, R 1, R 2, m and n are as defined herein, which are active as inhibitors of S-Nitrosoglutathione reductase (GSNOR). These compounds prevent, inhibit, or suppress the action of GSNOR and are therefore useful in the treatment of GSNOR mediated diseases, disorders, syndromes or conditions such as, e.g., pulmonary hypertension, acute respiratory distress syndrome (ARDS), asthma, bronchospasm, cough, pneumonia, pulmonary fibrosis, interstitial lung diseases, cystic fibrosis and chronic obstructive pulmonary disease (COPD).
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Page/Page column 57; 143
(2016/05/02)
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- Cs2CO3 as a source of carbonyl and ethereal oxygen in a Cu-catalysed cascade synthesis of benzofuran [3,2-: C] quinolin-6[5- H] ones
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The simultaneous construction of C-C, C-O, and C-N bonds utilizing Cs2CO3 as a source of both carbonyl (CO) and ethereal oxygen and a cascade synthesis of benzofuro[3,2-c]quinolin-6(5H)-one have been achieved using a combination of C
- Ali, Wajid,Modi, Anju,Behera, Ahalya,Mohanta, Prakash Ranjan,Patel, Bhisma K.
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supporting information
p. 5940 - 5944
(2016/07/06)
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- Copper-catalyzed annulation of α-substituted diazoacetates with 2-ethynylanilines: The direct synthesis of C2-functionalized indoles
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Copper-catalyzed direct annulation of α-substituted diazoacetates with 2-ethynylanilines leading to C2-functionalized indoles was achieved under mild reaction conditions. The C2-(carboxylate methyl) substituted indoles were obtained in moderate to high yi
- Liu, Gang,Xu, Guangyang,Li, Jian,Ding, Dong,Sun, Jiangtao
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p. 1387 - 1390
(2014/03/21)
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- [Cp*IrCl2]2 catalyzed formation of 2,2′-biindoles from 2-ethynylanilines
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[Cp*IrCl2]2 catalyzes the cyclization of 2-ethynylanilines to 2,2′-biindoles via intramolecular hydroamination. A reaction pathway has been proposed on the basis of deuterium labeling experiments and computational studies.
- Kumaran, Elumalai,Fan, Wai Yip,Leong, Weng Kee
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p. 1342 - 1345
(2014/04/03)
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- Flexible and practical synthesis of 3-oxyindoles through gold-catalyzed intermolecular oxidation of o-ethynylanilines
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A novel gold-catalyzed intermolecular oxidation of o-ethynylanilines has been developed. A range of functionalized 3-oxyindoles are readily accessed by utilizing this strategy. Importantly, this gold-catalyzed oxidative process outcompetes the typical ind
- Shu, Chao,Li, Long,Xiao, Xin-Yu,Yu, Yong-Fei,Ping, Yi-Fan,Zhou, Jin-Mei,Ye, Long-Wu
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supporting information
p. 8689 - 8692
(2014/07/22)
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- Copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N, O -acetal leading to construction of quinoline derivatives
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A novel copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N,O-acetal, which functioned as a C1 part, leading to the preparation of quinoline derivatives with an ester substituent on the 2-position is described. A combination of CuBr2/
- Sakai, Norio,Tamura, Kosuke,Shimamura, Kazuyori,Ikeda, Reiko,Konakahara, Takeo
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supporting information; experimental part
p. 836 - 839
(2012/04/05)
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- Formation of indoles, dihydroisoquinolines, and dihydroquinolines by ruthenium-catalyzed heterocyclizations
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Indoles, dihydroisoquinolines, and dihydroquinolines were efficiently prepared by ruthenium-catalyzed heterocyclizations of aromatic homo- and bis-homopropargyl amines/amides in the presence of an amine/ammonium base-acid pair. These regioselective 5-endo and 6-endo cyclizations most probably occur by nucleophilic trapping of key ruthenium-vinylidene intermediates. Georg Thieme Verlag Stuttgart · New York.
- Varela-Fernández, Alejandro,Varela, Jesús A.,Saá, Carlos
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p. 3285 - 3295
(2013/01/15)
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- Ruthenium-catalyzed cycloisomerization of aromatic homo- and bis-homopropargylic amines/amides: Formation of indoles, dihydroisoquinolines and dihydroquinolines
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Ruthenium-catalyzed cycloisomerizations of aromatic homo- and bis-homopropargylic amines/amides efficiently afford indoles, dihydroisoquinolines and dihydroquinolines. These processes were regioselective (5- and 6-endo cyclizations) on using key Ru vinylidene intermediates. The presence of an amine/ammonium base-acid pair increased the rate of cyclization and facilitated the catalytic turnover. Copyright
- Varela-Fernandez, Alejandro,Varela, Jesus A.,Saa, Carlos
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p. 1933 - 1937
(2011/10/08)
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- One-pot/four-step/palladium-catalyzed synthesis of indole derivatives: The combination of heterogeneous and homogeneous systems
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One-pot, four-step syntheses of indoles using both solid-supported heterogeneous and homogeneous palladium catalysts and reagents were carried out. Such a combination of these two-phase catalysts and reagents causes a dramatic increase in yield, and it is a simple process. The presented methodology is effective for four-step reactions to provide various functionalized indoles.
- Sakai, Hayato,Tsutsumi, Ken,Morimoto, Tsumoru,Kakiuchia, Kiyomi
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supporting information; experimental part
p. 2498 - 2502
(2009/08/14)
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- Rhodium-catalyzed cycloisomerization: Formation of indoles, benzofurans, and enol lactones
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(Chemical Equation Presented) Internal affairs: Indoles, benzofurans, and enol lactones are formed chemoselectively from the rhodium-catalyzed cyclo-isomerization reaction of easily prepared alkynyl aniline substrates (see scheme, cod = cycloocta-1,5-diene, DMF = N,N-dimethylformamide). The reaction may proceed by nucleophilic capture of a vinylidene intermediate. Indoles are formed under mild conditions using low catalyst loadings.
- Trost, Barry M.,McClory, Andrew
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p. 2074 - 2077
(2008/02/14)
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- Direct synthesis of polysubstituted quinoline derivatives by InBr 3-promoted dimerization of 2-ethynylaniline derivatives
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InBr3 promotes the dimerization of 2-ethynylaniline derivatives containing an unsubstituted terminal carbon leading to the production of polysubstituted quinoline derivatives in good yield.
- Sakai, Norio,Annaka, Kimiyoshi,Konakahara, Takeo
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p. 3653 - 3655
(2007/10/03)
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- Stereoselective synthesis of (E)-3-(methoxycarbonyl)methylene-1,3-dihydroindol-2-ones by palladium-catalyzed oxidative carbonylation of 2-ethynylanilines
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A direct synthesis of (E)-3-(methoxycarbonyl)methylene-1,3-dihydroindol-2-ones 2 by palladium-catalyzed oxidative carbonylation of 2-ethynylanilines 1 is reported. Reactions were carried out in MeOH as the solvent at 50-70°C in the presence of catalytic a
- Gabriele, Bartolo,Salerno, Giuseppe,Veltri, Lucia,Costa, Mirco,Massera, Chiara
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p. 4607 - 4613
(2007/10/03)
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