- Synthesis of a bifunctional boron-Lewis acid and studies on host-guest chemistry using pyridine and TMPD
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Based on the previously described bifunctional Lewis acid with a functional distance of the boron functions of 4.918(2) ?, the development of a further bifunctional, boron-containing Lewis acid with a wider functional distance is demonstrated. Again, a st
- Mitzel, Norbert W.,Neumann, Beate,Rudlof, Jens,Stammler, Hans-Georg
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- Synthesis of Chiral Triazole-Based Halogen Bond Donors
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The number of applications that use halogen bonding in the fields of self-assembly, supramolecular aggregation, and catalysis is growing. However, the accessibility of chiral halotriazoles shows that there is still a lot more to explore. The simple click-chemistry is applied for the straightforward synthesis of enantiomerically pure mono- and bidentate as well as multifunctional iodotriazole-based XB donors. The methodology is characterized by a wide variability due to easy access of chiral azides.
- Kaasik, Mikk,Kaabel, Sandra,Kriis, Kadri,J?rving, Ivar,Kanger, T?nis
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supporting information
p. 2128 - 2135
(2019/05/10)
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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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- Symmetric molecules with 1,4-triazole moieties as potent inhibitors of tumour-associated lactate dehydrogenase-A
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A series of symmetric molecules incorporating aryl or pyridyl moieties as central core and 1,4-substituted triazoles as a side bridge was synthesised. The new compounds were investigated as lactate dehydro-genase (LDH, EC 1.1.1.27) inhibitors. The cancer associated LDHA isoform was inhibited with IC50 = 117–174?μM. Seven compounds exhibited better LDHA inhibition (IC50 117–136?μM) compared to known LDH inhibitor–galloflavin (IC50 157?μM).
- Altamimi, Abdul-Malek S.,Abdel-Gawad, Sherif A.,Alafeefy, Ahmed M.,Balode, Agnese,Vozny, Igor,Pustenko, Aleksandrs,?alubovskis, Raivis,El Shikh, Mohey Eldin,Alasmary, Fatmah A. S.
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p. 147 - 150
(2018/01/02)
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- Control of supramolecular nanoassemblies by tuning the interactions of bent-shaped rod-coil molecules
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Rod-coil molecules 1a, 1b and 2a, 2b, consisting of biphenyl and phenyl units connected by an acetylene bond as the rod segment and oligo(ethylene glycol) (OEG) as the coil segment, were synthesized and characterized. Molecules 1a and 1b incorporate a but
- You, Shengnan,Zhong, Keli,Jin, Long Yi
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p. 3334 - 3340
(2017/07/10)
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- Amorphous formability and temperature-sensitive luminescence of lanthanide coordination glasses linked by thienyl, naphthyl, and phenyl bridges with ethynyl groups
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The glass-transition properties and temperature-sensitive luminescence of lanthanide (Ln(III)) coordination compounds are reported. The glass formability was systematically provided by incorporation of bent-angled phosphine oxide (2,5-bis-(diphenylphosphorylethynyl)thiophene: dpet, 2,7-bis(diphenylphosphorylethynyl)naphthalene: dpen, 1,3-bis(diphenylphosphorylethynyl)benzene: m-dpeb) ligands with thienyl, naphthyl, phenyl cores, and ethynyl groups. The glass-transition points were clearly identified for all Ln(III) coordination compounds (Tg = 65-87°C). The Tb(III)/Eu(III) mixed coordination glass [Tb,Eu(hfa)3(m-dpeb)]3 (hfa: hexafluoroacetylacetonate) also showed green, yellow, orange, and red photoluminescence depending on temperature.
- Hirai, Yuichi,Da Rosa, Pedro Paulo Ferreira,Nakanishi, Takayuki,Kitagawa, Yuichi,Fushimi, Koji,Hasegawa, Yasuchika
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supporting information
p. 322 - 326
(2017/05/09)
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- Method for synthesizing 1,3-diacetylene benzene
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The invention discloses a method for synthesizing 1,3-diacetylene benzene. The method comprises the following steps: a) taking m-phthalaldehyde and malonic acid as raw materials, catalyzing pyridine and carrying out a reaction in a first solvent to obtain
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Paragraph 0018
(2017/03/08)
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- Rapid access to unsymmetrical tolanes and alkynones by sequentially palladium-catalyzed one-pot processes
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Alkynones as well as unsymmetrically substituted tolanes (diarylalkynes) can be rapidly generated in a one-pot fashion via sequential palladium catalysis. Terminal alkynes, formed in situ by protecting-group free palladium-catalyzed coupling of aryl iodides with ethynyl magnesium bromide, are subsequently transformed by Sonogashira coupling with aryl halides or aroyl chlorides to furnish unsymmetrically substituted alkynes in good to excellent yields.
- G?tzinger, Alissa C.,Müller, Thomas. J. J.
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supporting information
p. 3498 - 3500
(2016/04/19)
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- Synthesis of chiral 1,3-bis(1-(diarylphosphoryl)ethyl)-benzenes via Ir-catalyzed double asymmetric hydrogenation of bis(diarylvinylphosphine oxides)
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A class of chiral 1,3-bis(diarylphosphinoethyl)benzenes, which are key intermediates for the synthesis of PCP-type chiral pincer ligands, were prepared in high diastereomeric ratios and excellent ee values via double asymmetric hydrogenation of the corresponding bis(diarylvinylphosphine oxide) substrates using a SpinPhox/Ir(I) complex as the catalyst. The hydrogenation product 5a was readily transformed into the corresponding borane-protected chiral PCP-type pincer ligand 7a with high enantiomeric excess, exemplifying a viable synthetic route to optically active chiral PCP pincer ligands.
- Liu, Xu,Han, Zhaobin,Wang, Zheng,Ding, Kuiling
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p. 1073 - 1078
(2014/08/18)
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- Aerobic oxynitration of alkynes with tBuONO and TEMPO
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An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.
- Dutta, Uttam,Maity, Soham,Kancherla, Rajesh,Maiti, Debabrata
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supporting information
p. 6302 - 6305
(2015/02/19)
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- Expedient synthesis of SMAMPs via click chemistry
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A novel series of synthetic mimics of antimicrobial peptides (SMAMPs) containing triazole linkers were assembled using click chemistry. While only moderately active in buffer alone, an increase in antimicrobial activity against Staphylococcus aureus and Escherichia coli was observed when these SMAMPs were administered in the presence of mouse serum. One compound had minimum inhibitory concentrations (MICs) of 0.39 μg/mL and 6.25 μg/mL, respectively, and an HC50 of 693 μg/mL. These values compared favorably to peptide-based antimicrobials. A correlation between the net positive charge and SMAMP antimicrobial activity was observed. The triazole linker, an amide surrogate, was found to provide better antimicrobial activity against both S. aureus and E. coli when compared to other analogues.
- Fu, Tsung-Hao,Li, Yan,Thaker, Hitesh D.,Scott, Richard W.,Tew, Gregory N.
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supporting information
p. 841 - 845
(2013/10/01)
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- Synthesis and biological evaluation of new bis-indolone-N-oxides
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A series of bis-indolone-N-oxides, 1a-f, was prepared from bis(ethynyl)benzenes and o-halonitroaryls and studied for their in vitro antiplasmodial activities against Plasmodium falciparum and representative strains of bacteria and candida as well as for their cytotoxicity against a human tumor cell line (MCF7). They did not cause any haemolysis (300 μg mL-1). Of the synthesized bis-indolones, compound 1a had the most potent antiplasmodial activity (IC50 = 0.763 μmol L-1 on the FcB1 strain) with a selectivity index (CC50 MCF7/IC 50 FcB1) of 35.6. No potency against the tested microbial strains was observed.
- Najahi, Ennaji,Valentin, Alexis,Tene, Nathan,Treilhou, Michel,Nepveu, Francoise
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- Intramolecular hydrogen bonds preorganize an aryl-triazole receptor into a crescent for chloride binding
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Figure presented Aryl-triazole pentads have been preorganized with intramolecular hydrogen bonds to enhance chloride binding. This outcome highlights the dual hydrogen bond donor and acceptor properties of 1,2,3-triazoles.
- Lee, Semin,Hua, Yuran,Park, Hyunsoo,Flood, Amar H.
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supporting information; experimental part
p. 2100 - 2102
(2010/06/20)
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- Thieme Chemistry Journal Awardees - Where are they now? A general one-step synthesis of alkynes from enolisable carbonyl compounds
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Terminal and internal acetylenes were obtained in good to excellent isolated yields from carbonyl compounds by converting the carbonyl functionality into the enol nonaflate intermediate followed by elimination to give the C-C triple bond. The one-pot transformations were uniformly induced by phosphazene bases combined with mildly electrophilic nonafluorobutane-1-sulfonyl fluoride. The method is the most general among those reported to date as it applies to both acyclic ketones and aldehydes. Only moderate kinetic regioselectivity in favour of alk-1-yne achieved from methyl n-alkyl ketone represents a limitation of the method. In all the other instances, individual acetylenic products were obtained. Georg Thieme Verlag Stuttgart.
- Lyapkalo, Ilya M.,Vogel, Michael A. K.,Boltukhina, Ekaterina V.,Vav?ík, Ji?í
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scheme or table
p. 558 - 561
(2009/07/09)
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- Counting the monomers in nanometer-sized oligomers by pulsed electron-electron double resonance
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In a lot of cases active biomolecules are complexes of higher order, thus methods capable of counting the number of building blocks and elucidating their geometric arrangement are needed. Therefore, we experimentally validate here spin-counting via 4-puls
- Bode, Bela E.,Margraf, Dominik,Plackmeyer, Joern,Duerner, Gerd,Prisner, Thomas F.,Schiemann, Olav
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p. 6736 - 6745
(2008/02/09)
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- Single-site modifications and their effect on the folding stability of m-phenylene ethynylene oligomers
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(Equation presented) The folded structure of a m-phenylene ethynylene oligomer is tolerant to single-site modifications to both the backbone sequence and end groups. The helical structure is reinforced by multiple noncovalent interactions, allowing the ol
- Goto, Hirofumi,Heemstra, Jennifer M.,Hill, David J.,Moore, Jeffrey S.
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p. 889 - 892
(2007/10/03)
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- Synthesis of terminal-biradical compounds consisting of two N-oxyl groups connected with conjugated π-systems
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Terminal-biradical compounds 1 having two N-oxyl groups connected with conjugated π-systems were synthesized by (1) addition of magnesium acetylide to 4-oxo-TEMPO, followed by dehydration, or (2) cross-coupling between acetylene and vinyl triflate derived from 4-oxo-TEMPO.
- Torii, Sigeru,Hase, Tomoyuki,Kuroboshi, Manabu,Amatore, Christian,Jutand, Anny,Kawafuchi, Hiroyuki
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p. 7391 - 7394
(2007/10/03)
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- The 'Inverse Electron-demand' Diels-Ader Reaction in Polymer Synthesis. Part 1. A Convenient Synthetic Route to Diethynyl Aromatic Compounds
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The simple procedure whereby acetophenone derivatives are converted, by reaction with phosphoryl chloride and N,N-dimethylformamide, into β-chlorocinnamaldehydes, and thence, by base-induced elimination, into ethynylarenes, has been extended to diketones of the type MeCOC6H4COMe (m- and p-) and (p-MeCOC6H4)2X (X = O, S, SO2, CH2, CO, or a single bond): the corresponding diethynyl compounds are obtained by this route in acceptable yield. 1,3,5-Triacetylbenzene is similarly converted into 1,3,5-triethynylbenzene.
- Royles, Brodyck J. L.,Smith, David M.
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p. 355 - 358
(2007/10/02)
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- A CONVENIENT PROCEDURE FOR THE SYNTHESIS OF BIS(ETHYNYL)BENZENE DERIVATIVES
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A convenient two-step synthesis of bis(ethynyl)benzenes starting from the corresponding bis(acetyl)derivatives via chlorination of the carbonyl functions with PCl5 followed by dehydrochlorination with sodium amide in liquid ammonia is described.The new compounds obtained have been characterised by spectroscopic and elemental analysis.
- Ortaggi, Giancarlo,Sleiter, Giancarlo,D'Ilario, Lucio,Bolasco, Adriana,Chimenti, Franco
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p. 319 - 322
(2007/10/02)
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- Synthesis of High Carbon Materials from Acetylenic Precursors. Preparation of Aromatic Monomers Bearing Multiple Ethynyl Groups
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The synthesis of polyethynyl aromatics as starting materials for the preparation of highly cross-linked organic solids containing high atom fractions of carbon is described.Treatment of bromo- and iodoaromatic compounds with (trimethylsilyl)acetylene (TMSA) in the presence of palladium(O) and copper(I) in amine solvents yields (trimethylsilyl)ethynyl-substituted aromatics.The TMS protecting groups can be removed by hydrolysis with mild base.Compounds prepared by using this technique include 1,3-diethynylbenzene, 2,5-diethynylthiophene, 1,3-diethynyltetrafluorobenzene, 1,4-diethynyltetrafluorobenzene, 2-ethynylthiazole, 2,4-diethynylthiazole, 2,7-diethynylnaphthalene, hexakis((trimethylsilyl)ethynyl)benzene, tetraethynylthiophene, 2,5-bis((trimethylsilyl)ethynyl)-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene, 2,5-diethynyl-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene, 2,5-bis(4-(2-thienyl)butadiynyl)-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene, and 2,5-bis-(4-(2-thienyl)butadiynyl)-3,4-diethynylthiophene.
- Neenan, Thomas X.,Whitesides, George M.
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p. 2489 - 2496
(2007/10/02)
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- Process for the preparation of bromoarylacetylene and aryldiacetylene precursors
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Bromoarylacetylenes such as m-bromophenylacetylene and certain precursors to such bromoarylacetylene are prepared by reacting an aryldibromide with a substituted terminal acetylene compound containing at least three carbon atoms and a hydroxy group on the carbon atom adjacent to the acetylene group in the presence of a dialkyl or trialkyl amine solvent and a catalyst system consisting of a palladium complex containing two halogen moieties and two tri-substituted phosphine moieties. Additional triphenylphosphine can be added. A cuprous iodide promoter is also employed in the reaction sequence. The bromoarylacetylenes can be reacted with a substituted terminal acetylene compound as defined using the same catalyst system as defined to produce the corresponding aryldihydroxy substituted acetylenes. Certain bromophenylhydroxy substituted acetylenes are claimed as new compositions.
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