- Layer-type organosilver(I) complexes assembled with nitrate and functionalized phenylethynide ligands
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A series of seven silver(I) nitrate complexes containing new ligands each composed of a functionalized phenyl nucleus bearing a terminal ethynyl substituent has been synthesized and characterized by single-crystal X-ray analysis. The coordination preferen
- Cheng, Ping-Shing,Hau, Sam C.K.,Mak, Thomas C.W.
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Read Online
- Synthesis of alkynes under dry reaction conditions
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An easy synthetic method was developed under dry reaction conditions for the preparation of terminal alkynes from 1,1-dibromoalkenes and in the presence of succinimide which acts as a nucleophile and proton donor. It was demonstrated with the synthesis of a broad spectrum of terminal alkynes and extended to synthesize internal alkynes under tandem reaction conditions.
- Rao, Maddali L.N.,Shamim Islam, Sk
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supporting information
(2021/04/19)
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- Rhodium-catalysed: Ortho -alkynylation of nitroarenes
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The ortho-alkynylation of nitro-(hetero)arenes takes place in the presence of a Rh(iii) catalyst to deliver a wide variety of alkynylated nitroarenes regioselectively. These interesting products could be further derivatized by selective reduction of the nitro group or palladium-catalysed couplings. Experimental and computational mechanistic studies demonstrate that the reaction proceeds via a turnover-limiting electrophilic C-H metalation ortho to the strongly electron-withdrawing nitro group. This journal is
- Echavarren, Antonio M.,García-Morales, Cristina,Mayans, Joan Guillem,Montesinos-Magraner, Marc,Tan, Eric
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p. 14731 - 14739
(2021/12/02)
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- 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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- 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 33
(2019/05/15)
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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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- Design, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs
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Research on thymidylate synthase inhibitors has been a hot spot for anticancer drug development. Here, based on the structures and pharmacological properties of two types of TS inhibitors, through a molecular assembly principle of drugs design, we designed and synthesized a series of 30 novel uracil derivatives as TS inhibitors. The antiproliferative ability of these compounds was evaluated against four cancer cell lines (A549, OVCAR-3, SGC-7901, and HepG2) by the MTT assay. Most of them showed excellent activities against all the tested cell lines. Furthermore, hTS assay results showed that these compounds have the unique ability to inhibit hTS activity in vitro. Notably, compound 13j exhibited the most potent activity against A549 cells (IC50 = 1.18 μM) and extremely prominent enzyme inhibition (IC50 = 0.13 μM), which was superior to the pemetrexed (PTX, IC50 = 3.29 μM and IC50 = 2.04 μM). Flow cytometric analysis showed the compound 13j could inhibit A549 cells proliferation by arresting the cell cycle in the G1/S phase, then induced the cell apoptosis. Further western blot analysis showed that compound 13j could down-regulate the cycle checkpoint proteins cyclin D1 and cyclin E to inhibit the cell cycle progression, and then induce intrinsic apoptosis by activating caspase-3, and reducing the ratio of bcl-2/bax. All of these results demonstrated that this new structure has potential drug-making properties and provides new ideas for drug development.
- Lu, Guo-qing,Li, Xin-yang,Mohamed O, Kamara,Wang, Depu,Meng, Fan-hao
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p. 282 - 296
(2019/03/27)
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- DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes
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Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).
- Thummala, Yadagiri,Karunakar, Galla V.,Doddi, Venkata Ramana
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supporting information
p. 611 - 616
(2019/01/04)
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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 0378-0379
(2018/08/29)
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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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- 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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- 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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- 1,2,3-triazole compounds with antitumor activity and preparation method for 1,2,3-triazole compounds
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The present invention relates to three 1,2,3-triazole compounds with aryl structures on the left sides, and the general structural formulae thereof are as shown in the specification. The three compounds have good antitumor activity.
- -
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Paragraph 0084; 0085
(2016/10/10)
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- The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity
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The dual role of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was demonstrated in a synthesis of terminal aryl- and styryl-acetylenes. Mechanistically, a tandem process involving elimination/Umpolung/protonation occurs in a single step to generate terminal aryl- and styryl-acetylenes from geminal dibromoalkenes. The key to the success of this transformation lies in the organobase-mediated generation of the acetylide from the 1-bromoalkynes at room temperature. The unique characteristics of DBU as an inherently safer reagent make it an attractive alternative to previous systems wherein required pyrophoric reagents and nonambient temperatures remain unsolved issues. The procedure does not work for the synthesis of alkyl-acetylenes.
- Morri, Ashok Kumar,Thummala, Yadagiri,Doddi, Venkata Ramana
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p. 4640 - 4643
(2015/09/28)
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- Dibenzonaphthyridinones: Heterocycle-to-Heterocycle Synthetic Strategies and Photophysical Studies
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A heterocycle-to-heterocycle strategy is presented for the preparation of highly fluorescent and solvatochromic dibenzonaphthyridinones (DBNs) via methodology that leads to the formation of a tertiary, spiro-fused carbon center. A linear correlation between the results of photophysical experiments and time dependent density functional theory calculations was observed for the λmax of excitation for DBNs with varying electronic character.
- Palazzo, Teresa A.,Patra, Digambara,Yang, Joung S.,El Khoury, Elsy,Appleton, Mackenzie G.,Haddadin, Makhluf J.,Tantillo, Dean J.,Kurth, Mark J.
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supporting information
p. 5732 - 5735
(2015/12/11)
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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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- Synthesis, characterization, and solid-state polymerization of cross-conjugated octatetraynes
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Two series of cross-conjugated 1,3,5,7-octatetraynes (1a-1l and 6a-6d) have been synthesized. UV-vis spectroscopic analysis shows that pendent groups connected to the cross-conjugated skeleton have little effect on the λmax energies, irrespective of whether the groups are electron withdrawing or donating. A number of the isolated products readily give crystals suitable for X-ray crystallography, and the solid-state structural properties of five derivatives (1k, 1l, 6a, 6c, and 6d) have been examined by X-ray crystallographic analysis. Parallel packing of the polyynes in the solid state indicates that four of the five samples are potentially suitable for topochemical polymerization, based on solid-state packing parameters θ, R, and d. Attempts to effect a solid-state reaction have been explored through UV-vis and γ-ray irradiation as well as thermal heating. The course of these reactions was monitored by differential scanning calorimetry (DSC) analysis, as well as UV-vis and solid-state 13C NMR spectroscopy (for 1d, 1j, 1k, and 6d), which offered evidence of polymer formation from these reactions. Structural determination of the product(s), however, remains elusive.
- Zhao, Yuming,Luu, Thanh,Bernard, Guy M.,Taerum, Tyler,McDonald, Robert,Wasylishen, Roderick E.,Tykwinski, Rik R.
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p. 994 - 1014
(2013/02/22)
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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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- 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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- One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from aldehydes and amines
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A one-pot, three-step synthesis of 1,4-disubstituted 1,2,3-triazoles from aldehyde and amine has been developed by in situ transformation of aldehyde into alkyne, followed by diazo-transfer of amine into azide and subsequent cycloaddition. This procedure allowed the synthesis of fluorescent amino acid derivatives as well as glycoconjugate mimetics. Georg Thieme Verlag Stuttgart.
- Maisonneuve, Stephane,Xie, Juan
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experimental part
p. 2977 - 2981
(2010/01/21)
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- Solid-state polymerization of monophenylbutadiyne derivatives
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Solid-state polymerization of phenylbutadiyne derivatives with o-nitro, m-nitro or p-nitro group was investigated. All monomers in bulk crystals could be thermally polymerized to become black suggesting formation of extended pi-conjugation system. However, no regular polydiacetylene structures were confirmed by the structural analysis. Nanocrystals of the m-nitro derivative were prepared, and the different polymerization behavior compared with in the bulk crystals was observed. Copyright Taylor & Francis Group, LLC.
- Watanabe, Jun-Ichi,Yokoyama, Harumi,Okada, Shuji,Takaragi, Shigeru,Matsuda, Hiro,Nakanishi, Hachiro
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p. 441 - 447
(2011/11/07)
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- Terminal alkynes from aldehydes via dehydrohalogenation of (Z)-1-iodo-1-alkenes with TBAF
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Terminal alkynes were prepared in near quantitative yields via dehydrohalogenation of (Z)-1-iodo-1-alkenes with tetrabutylammonium fluoride (TBAF) under mild conditions. The methodology was expanded to include a one-pot, direct synthesis of terminal alkynes from aldehydes without the necessity of isolating and purifying the intermediate iodoalkene.
- Beshai, Mira,Dhudshia, Bhartesh,Mills, Ryan,Thadani, Avinash N.
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supporting information; experimental part
p. 6794 - 6796
(2009/04/07)
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- One-pot synthesis of monosubstituted aryl(hetaryl)acetylenes by direct introduction of the C≡CH residue into arenes and hetarenes
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A convenient one-pot synthesis of aryl(hetaryl)acetylenes by cross-coupling of aryl(hetaryl)iodides with acetylene in presence of PdCl2(Ph 3)2, CuI and K2CO3 in DMF has been developed.
- Vasilevsky, Sergei F.,Klyatskaya, Svetlana V.,Elguero, José
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p. 6685 - 6688
(2007/10/03)
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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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- Microwave-assisted in situ deprotection and ω-methoxylation of TMS-protected aryl alkynes
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Using microwave technology, rapid ω-methoxylation of aryl alkynes is possible.
- Wettergren, Jenny,Minidis, Alexander B. E.
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p. 7611 - 7612
(2007/10/03)
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- Preparation of 2′-aminoacetophenones: A one-pot hydration and reduction of 1-ethynyl-2-nitrobenzenes
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The reductive hydration of 1-ethynyl-2-nitrobenzenes to the corresponding 2′-aminoacetophenones with a range of common reducing agents is described.
- Bosch, Eric,Jeffries, Laura
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p. 8141 - 8142
(2007/10/03)
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- Synthesis of the Substituted Z-1-Bromo-1-alkenes and Arylacetylenes from 2,3-Dibromocarboxylic Acids
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Stereoselectivity was studied of simultaneous debromination-decarboxylation of dibrominated cinnamic and acrylic acids. The best selectivity in formation of Z-vinyl bromides was achieved with the use of organic nitrogen bases. The 1-bromo-1-alkenes were converted into the corresponding acetylenes.
- Matveeva,Erin,Kurz
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p. 1065 - 1067
(2007/10/03)
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- Quinazoline antifolate thymidylate synthase inhibitors: γ-linked L-D, D- D, and D-L dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8- dideazafolic acid (ICI 198583)
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The syntheses of γ-linked L-D, D-D, and D-L dipeptide analogues of 2- desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583) are described. The general methodology for the synthesis of these molecules involved the preparation of the dipeptide derivatives employing solution phase peptide synthesis followed by condensation of the dipeptide free bases with the appropriate pteroic acid analogue via diethyl cyanophosphoridate (DEPC) activation. In the final step, tert-butyl esters were removed by trifluoroacetic acid (TFA) hydrolysis. Z-L-Glu-OBu(t)-γ-D-Ala-OBu(t), for example, was prepared from α-tert-butyl N-(benzyloxycarbonyl)-L-glutamate and tert-butyl D-alaninate via isobutyl-mixed anhydride coupling. The Z- group was removed by catalytic hydrogenolysis and the resulting dipeptide free base condensed with 2-desamino-2-methyl-N10-propargyl-5,8- dideazapteroic acid via DEPC coupling. Finally, tert-butyl esters were removed by TFA hydrolysis to give ICI 198583-γ-D-Ala. The compounds were tested as inhibitors of thymidylate synthase and L1210 cell growth. Good enzyme and growth inhibitory activity were found with y-linked L-D dipeptides, the best examples being the Glu-γ-D-Glu derivative 35 (K(i) = 0.19 nM, L1210 IC50 = 0.20 ± 0.017 μM) and the Glu-γ-D-α-aminoadipate derivative 39 (K(i) = 0.12 nM, L1210 IC50 = 0.13 ± 0.063 μM). In addition, ICI 198583 L-γ-D-linked dipeptides were resistant to enzymatic degradation in mice.
- Bavetsias,Jackman,Kimbell,Gibson,Boyle,Bisset
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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)
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- Prototypes for the polaronic ferromagnet. Synthesis and characterization of high-spin organic polymers
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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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- ACETYLENIC FRAGMENTATION OF ACYL DERIVATIVES OF THE FISCHER BASE
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Indolenium salts, which readily undergo cleavage in aqueous alkali to give a monosubstituted acetylene and 1,3,3-trimethyl-2-oxindole, are formed when acyl derivatives of the Fischer base are heated with phosphorus oxychloride.Various aryl- and hetarylacetylenes can be conveniently obtained by this method.
- Prizhiyalgovskaya, N. M.,Kon'kov, L. I.,Tarshits, D. L.,Salmina, S. V.,Segizova, N. T.,Suvorov, N. N.
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p. 751 - 754
(2007/10/02)
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