cas 80673-00-3, 3-(TRIMETHYLSILYLETHYNYL)PYRIDINE

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One-pot synthesis of dihydropyridine carboxylic acids via functionalization of 3-((trimethylsilyl)ethynyl)pyridines and an unusual hydration of alkynes: Molecular docking and antifungal activity
Activation of 3-((trimethylsilyl)ethynyl)pyridine with triflic anhydride followed by nucleophilic addition of bis(trimethylsili) ketene acetals and a unusual alkyne hydration allowed to obtain new series of 3-acetylated dihydropyridine acids 3a-h in a sin
Ballinas-Indilí, Ricardo,Gómez-García, Omar,Trevi?o-Crespo, Eric,Andrade-Pavón, Dulce,Villa-Tanaca, Lourdes,Toscano, Ruben A.,álvarez-Toledano, Cecilio
(2021)
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Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block
A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.
Varga, Bálint,Tóth, Balázs L.,Béke, Ferenc,Csenki, János T.,Kotschy, András,Novák, Zoltán
supporting information
p. 4925 - 4929
(2021/07/01)

Synthesis, Electrochemistry, and Optical Properties of Highly Conjugated Alkynyl-Ferrocenes and -Biferrocenes
Sonogashira reactions are utilized herein to react iodo-ferrocenes and -biferrocenes with terminal alkyne ligands, functionalized with both pyridine and thioanisole groups. High-yielding reactions generate both monoalkynyl and dialkynyl derivatives, the r
Bennett, Troy L. R.,Wilkinson, Luke A.,Lok, Jasmine M. A.,O'Toole, Robert C. P.,Long, Nicholas J.
p. 1156 - 1162
(2021/05/06)

Novel Class of Colony-Stimulating Factor 1 Receptor Kinase Inhibitors Based on an o-Aminopyridyl Alkynyl Scaffold as Potential Treatment for Inflammatory Disorders
Colony-stimulating factor 1 receptor (CSF-1R) is involved in inflammatory disorders as well as in many types of cancer. Based on high-throughput screening and docking results, we performed a detailed structure-activity-relationship study, leading to the d
Xie, Zhicheng,Wu, Bing,Liu, Yingqiang,Ren, Wenming,Tong, Linjiang,Xiang, Caigui,Wei, Aihuan,Gao, Yuanzhuo,Zeng, Limin,Xie, Hua,Tang, Wei,Hu, Youhong
p. 1397 - 1414
(2020/02/04)

Sustainable Ligand-Free Heterogeneous Palladium-Catalyzed Sonogashira Cross-Coupling Reaction in Deep Eutectic Solvents
The commercially available and cheap Pd/C was found to promote Sonogashira couplings in the environmentally friendly choline chloride/glycerol eutectic mixture in the absence of external ligands. Under heterogeneous conditions, (hetero)aryl iodides were successfully coupled with both aromatic and aliphatic alkynes in yields ranging from 50 to 99 % within 3 h at 60 °C. The aforementioned catalytic system proved to be effective also towards electron-rich iodides, which are notoriously known to be poorly reactive in Pd-catalyzed Sonogashira coupling reactions. The eutectic mixture and the catalyst could easily and successfully be recycled up to four times with an E-factor as low as 24.4.
Messa, Francesco,Dilauro, Giuseppe,Perna, Filippo M.,Vitale, Paola,Capriati, Vito,Salomone, Antonio
p. 1979 - 1984
(2020/02/20)

RET INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
Provided herein are a RET inhibitor, a pharmaceutical composition thereof and uses thereof. In particular, provided is a compound having Formula (I) or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof. Provided is a pharmaceutical composition comprising the compound, and uses of the compound and pharmaceutical composition thereof for the preparation of a medicament, in particular for treatment and prevention of RET-related diseases and conditions, including cancer, irritable bowel syndrome, and/or pain associated with irritable bowel syndrome.
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(2020/07/05)

Design and characterization of a heterocyclic electrophilic fragment library for the discovery of cysteine-targeted covalent inhibitors
A fragment library of electrophilic small heterocycles was characterized through cysteine-reactivity and aqueous stability tests that suggested their potential as covalent warheads. The analysis of theoretical and experimental descriptors revealed correlations between the electronic properties of the heterocyclic cores and their reactivity against GSH that are helpful in identifying suitable fragments for cysteines with specific nucleophilicity. The most important advantage of these fragments is that they show only minimal structural differences from non-electrophilic counterparts. Therefore, they could be used effectively in the design of targeted covalent inhibitors with minimal influence on key non-covalent interactions.
Keeley,ábrányi-Balogh,Keseru
supporting information
p. 263 - 267
(2019/03/05)

Et2Zn-mediated stoichiometric C(sp)-H silylation of 1-alkynes and chlorosilanes
A first example of an Et2Zn mediated silylation of 1-aklynes is reported. A series of functional groups are tolerated in this reaction. Mechanistic studies support Zn alkynilides as intermediates in the reaction. This reaction protocol provides a practical method for the preparation of alkynylsilanes and expands the application of organometallic zinc in organic synthesis.
Huang, Pan,Xu, Dawen,Reich, Robert M.,Kaiser, Felix,Liu, Boping,Kühn, Fritz E.
supporting information
p. 1574 - 1577
(2019/05/17)

Catalytic Activation of Trimethylsilylacetylenes: A One-Pot Route to Unsymmetrical Acetylenes and Heterocycles
For the synthesis of unsymmetrical acetylenes, a Sonogashira coupling-deprotection-Sonogashira coupling reaction sequence is often used. Removal of protecting groups requires harsh conditions or an excess of difficult to handle and expensive reagents. Herein, we disclose a novel catalytic method for the selective deprotection of trimethylsilylacetylenes in Sonogashira reaction. The reagent hexafluorosilicic acid, an inexpensive nontoxic compound, was used to promote the selective desilylation. This method enables the efficient synthesis of unsymmetric acetylenes with other silylated functional groups present. Further possibilities of the method were explored by synthesis of heterocycles.
Lasányi, Dániel,Mészáros, ádám,Novák, Zoltán,Tolnai, Gergely L.
p. 8281 - 8291
(2018/06/11)

Small Molecule Inhibitors Simultaneously Targeting Cancer Metabolism and Epigenetics: Discovery of Novel Nicotinamide Phosphoribosyltransferase (NAMPT) and Histone Deacetylase (HDAC) Dual Inhibitors
Cancer metabolism and epigenetics are among the most intensely pursued research areas in anticancer drug discovery. Here we report the first small molecules that simultaneously inhibit nicotinamide phosphoribosyltransferase (NAMPT) and histone deacetylase (HDAC), two important targets of cancer metabolism and epigenetics, respectively. Through iterative structure-based drug design, chemical synthesis, and biological assays, a highly potent dual NAMPT and HDAC inhibitor was successfully identified. Compound 35 possessed excellent and balanced activities against both NAMPT (IC50 = 31 nM) and HDAC1 (IC50 = 55 nM). It could effectively induce cell apoptosis and autophagy and ultimately led to cell death. Importantly, compound 35 showed excellent in vivo antitumor efficacy in the HCT116 xenograft model. This proof-of-concept study demonstrates the feasibility of discovering an inhibitor targeting cancer metabolism and epigenetics and provides an efficient strategy for multitarget antitumor drug discovery.
Dong, Guoqiang,Chen, Wei,Wang, Xia,Yang, Xinglin,Xu, Tianying,Wang, Pei,Zhang, Wannian,Rao, Yu,Miao, Chaoyu,Sheng, Chunquan
p. 7965 - 7983
(2017/10/18)

PALLADIUM COMPLEX, COUPLING REACTION USING THE PALLADIUM COMPLEX AND METHOD FOR PRODUCING ORGANIC ALKYNE COMPOUND USING THE COUPLING REACTION
PROBLEM TO BE SOLVED: To provide a novel palladium catalyst which can be used for synthesis of an organic alkyne compound, using an arylation agent having an ester group in place of halogenated aryl. SOLUTION: The present invention provides a palladium co
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(2017/10/31)

Octahedral [Pd6L8]12+ Metallosupramolecular Cages: Synthesis, Structures and Guest-Encapsulation Studies
Four planar tripyridyl ligands (Ltripy), 1,3,5-tris(pyridin-3-ylethynyl)benzene 1 a, 1,3,5-tris[4-(3-pyridyl)phenyl]benzene 2 a, and the hexyloxy chain functionalized derivatives 1,3,5-tris[(3-hexyloxy-5-pyridyl)ethynyl]benzene 1 b, and 1,3,5-tris[4-(3-hexyloxy-5-pyridyl)phenyl]benzene 2 b, were synthesized and used to generate a family of [Pd6(Ltripy)8](BF4)12 octahedral cages (Ltripy=1 a, b or 2 a, b). The ligands and cages were characterized using a combination of 1H, 13C, and DOSY nuclear magnetic resonance (NMR) spectroscopy, high resolution electrospray mass spectrometry (HR-ESI-MS), infrared (IR) spectroscopy, elemental analysis, and in three cases, X-ray crystallography. The molecular recognition properties of the cages with neutral and anionic guests were examined, in dimethyl sulfoxide (DMSO), using NMR spectroscopy, mass spectrometry and molecular modeling. No binding was observed with simple aliphatic and aromatic guest molecules. However, anionic sulfonates were found to interact with the octahedral cages and the binding interaction was size selective. The smaller [Pd6(1 a, b)8]12+ cages were able to interact with three p-toluenesulfonate guest molecules while the larger [Pd6(2 a, b)8]12+ systems could host four of the anionic guest molecules. To probe the importance of the hydrophobic effect, a mixed water–DMSO (1:1) solvent system was used to reexamine the binding of the neutral organic guests adamantane, anthracene, pyrene and 1,8-naphthalimide within the cages. In this solvent system all the guests except adamantane were observed to bind within the cavities of the cages. NMR spectroscopy and molecular modeling indicated that the cages bind multiple copies of the individual guests (between 3–6 guest molecules per cage).
Kim, Tae Y.,Digal, Lori,Gardiner, Michael G.,Lucas, Nigel T.,Crowley, James D.
supporting information
p. 15089 - 15097
(2017/10/11)

Fluoroform-Derived CuCF3 for Trifluoromethylation of Terminal and TMS-Protected Alkynes
An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.
He, Lisi,Tsui, Gavin Chit
supporting information
p. 2800 - 2803
(2016/07/06)

Microwave-assisted copper- and palladium-catalyzed sonogashira-type coupling of aryl bromides and iodides with trimethylsilylacetylene
An efficient and rapid method was developed for the synthesis of 1-aryl-2-(trimethylsilyl)acetylene. Copper and palladium-catalyzed sonogashira-type coupling of trimethylsilylacetylene and aryl bromides or iodides in the presence of triethylamine as base
Lei, Yonghua,Hu, Tianhan,Wu, Xingsen,Wu, Yue,Xiang, Hua,Sun, Haopeng,You, Qidong,Zhang, Xiaojin
p. 1100 - 1103
(2016/03/09)

2,4,6-Triaminopyrimidine as a Novel Hinge Binder in a Series of PI3Kδ Selective Inhibitors
Inhibition of phosphoinositide 3-kinase δ (PI3Kδ) is an appealing target for several hematological malignancies and inflammatory diseases. Herein, we describe the discovery and optimization of a series of propeller shaped PI3Kδ inhibitors comprising a novel triaminopyrimidine hinge binder. Combinations of electronic and structural strategies were employed to mitigate aldehyde oxidase mediated metabolism. This medicinal chemistry effort culminated in the identification of 52, a potent and highly selective inhibitor of PI3Kδ that demonstrates efficacy in a rat model of arthritis.
Patel, Leena,Chandrasekhar, Jayaraman,Evarts, Jerry,Haran, Aaron C.,Ip, Carmen,Kaplan, Joshua A.,Kim, Musong,Koditek, David,Lad, Latesh,Lepist, Eve-Irene,McGrath, Mary E.,Novikov, Nikolai,Perreault, Stephane,Puri, Kamal D.,Somoza, John R.,Steiner, Bart H.,Stevens, Kirk L.,Therrien, Joseph,Treiberg, Jennifer,Villase?or, Armando G.,Yeung, Arthur,Phillips, Gary
p. 3532 - 3548
(2016/05/19)

Rapid and efficient desilylation and deuteration of alkynylpyridines
We describe a rapid and efficient technique for the direct installation of deuterium atoms following the removal of trimethylsilyl groups from alkynylpyridines. Utilizing tetrabutylammonium fluoride in the presence of deuterium oxide, we observe up to 97% deuterium incorporation in as little as one minute of reaction time.
Gelinas, Benjamin S.,Jaye, Joseph A.,Mattos, Gabriela R.,Fort, Eric H.
supporting information
p. 4232 - 4233
(2015/06/22)

Substituent parameters impacting isomer composition and optical properties of dihydroindolizine molecular switches
In an attempt to understand which factors influence constitutional isomer control of 6′- and 8′-substituted dihydroindolizines (DHIs), a series of asymmetric pyridines was condensed with dimethyl spiro[cycloprop[2] ene-1,9′-fluorene]-2,3-dicarboxylate. The substituents on the pyridial derivatives ranged from donating to withdrawing and demonstrated control over the isomeric ratios for all DHIs. Substituent control proved to be selective for the highly donating amino, which exclusively formed the 8′ isomer. The same ratios were reproduced via photolytic experiments, which suggested that the condensation reaction is dominated by the products thermodynamic stability. The electronic influences of the substituents extends beyond isomer control, as it impacts the DHIs optical properties and electrocyclization (switching) rates to the spiro conformers. Our results allow us to predict the syntheses and properties of future 6′- or 8′-substituted DHIs, molecules that will be applied in understanding the role of the dipole vector orientation to work function switching.
Bartucci, Matthew A.,Ciszek, Jacob W.
supporting information
p. 5586 - 5594
(2014/07/08)

Palladium and copper-supported on charcoal: A heterogeneous multi-task catalyst for sequential Sonogashira-Click and Click-Heck reactions
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
p. 78 - 85
(2014/03/21)

Pseudo five-component synthesis of 3-(hetero)arylmethyl-2,5-di(hetero)-aryl-substituted thiophenes via sonogashira-glaser cyclization sequence
The Sonogashira-Glaser sequence combined with a microwave-assisted cyclization is a powerful tool to synthesize unsymmetrically substituted conjugated thiophenes. A variety of 3-(hetero)arylmethyl-2,5-di(hetero)aryl-substituted thiophenes could be synthesized in moderate to excellent yields using a single Pd/Cu catalyst system. The presented method is strikingly simple to perform using commercially available starting materials. The obtained trisubstituted oligothiophene derivatives are interesting molecules for materials science.
Klukas, Fabian,Perkampus, J?rg,Urselmann, Dominik,Müller, Thomas J. J.
p. 3415 - 3422
(2015/02/02)

Cross-Metathesis of Terminal Alkynes
Terminal acetylenes are amongst the most problematic substrates for alkyne metathesis because they tend to undergo rapid polymerization on contact with a metal alkylidyne. The molybdenum complex 3 endowed with triphenylsilanolate ligands, however, is capable of inducing surprisingly effective cross-metathesis reactions of terminal alkyl acetylenes with propynyl(trimethyl)silane to give products of type R1-C≡CSiMe. This unconventional way of introducing a silyl substituent onto an alkyne terminus complements the conventional tactics of deprotonation/silylation and excels as an orthogonal way of alkyne protecting group chemistry for substrates bearing base-sensitive functionalities. Moreover, it is shown that even terminal aryl acetylenes can be cross-metathesized with internal alkyne partners. These unprecedented transformations are compatible with various functional groups. The need to suppress acetylene formation, which seems to be a particularly effective catalyst poison, is also discussed.
Lhermet, Rudy,Fürstner, Alois
supporting information
p. 13188 - 13193
(2016/02/19)

Rhenium(I) polypyridine diamine complexes as intracellular phosphorogenic sensors: Synthesis, characterization, emissive behavior, biological properties, and nitric oxide sensing
We report the development of a series of rhenium(I) polypyridine complexes appended with an electron-rich diaminoaromatic moiety as phosphorogenic sensors for nitric oxide (NO). The diamine complexes [Re(N^N)(CO)3(py-DA)] [PF6] (py-DA=3-(N-(2-amino-5-methoxyphenyl)aminomethyl)pyridine; N^N=1,10-phenanthroline (phen) (1a), 3,4,7,8-tetramethyl-1,10-phenanthroline (Me4-phen) (2a), 4,7-diphenyl-1,10-phenanthroline (Ph 2-phen) (3a)) have been synthesized and characterized. In contrast to common rhenium(I) diimines, these diamine complexes were very weakly emissive due to quenching of the triplet metal-to-ligand charge-transfer ( 3MLCT) emission by the diaminoaromatic moiety through photoinduced electron transfer (PET). Upon treatment with NO, the complexes were converted into the triazole derivatives [Re(N^N)(CO)3(py-triazole)][PF 6] (py-triazole=3-((6-methoxybenzotriazol-1-yl)methyl)pyridine; N^N=phen (1b), Me4-phen (2b), Ph2-phen (3b)), resulting in significant emission enhancement (I/I0≈60). The diamine complexes exhibited high reaction selectivity to NO, and their emission intensity was found to be independent on pH. Also, these complexes were effectively internalized by HeLa cells and RAW264.7 macrophages with negligible cytotoxicity. Additionally, the use of complex 3a as an intracellular phosphorogenic sensor for NO has been demonstrated. Emission turned ON for NO: A series of rhenium(I) polypyridine complexes functionalized with an electron-rich diaminoaromatic moiety has been developed as a new class of phosphorogenic sensors for NO. Upon treatment with NO, the weakly emissive complexes were converted into the strongly emissive triazole derivatives, resulting in significant emission enhancement (I/I0≈60; see figure). Experiments showed that the diamine complexes can sense NO that is 1) generated exogenously by NOC-7 in HeLa cells and 2) produced endogenously in RAW264.7 macrophages.
Choi, Alex Wing-Tat,Yim, Vicki Man-Wai,Liu, Hua-Wei,Lo, Kenneth Kam-Wing
supporting information
p. 9633 - 9642
(2014/08/18)

Aerobic oxynitration of alkynes with tBuONO and TEMPO
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
supporting information
p. 6302 - 6305
(2015/02/19)

Palladium-catalyzed trifluoroethylation of terminal alkynes with 1,1,1-trifluoro-2-iodoethane
An efficient Csp-CH2CF3 bond-forming reaction via Pd-catalyzed 2,2,2-trifluoroethylation of aryl and alkyl terminal alkynes has been developed. This protocol proceeds under mild conditions using the readily available and cheap reagent CF3CH2I as the source of the CH2CF3 group. Various terminal aryl alkynes as well as alkylacetylenes can be transformed into the corresponding trifluoroethylated products in good-to-excellent yields. The method is tolerant of carbonyl, nitro, ester, cyano, and even formyl groups.
Feng, Yi-Si,Xie, Chuan-Qi,Qiao, Wen-Long,Xu, Hua-Jian
supporting information
p. 936 - 939
(2013/03/28)

Rapid discovery of a novel series of Abl kinase inhibitors by application of an integrated microfluidic synthesis and screening platform
Drug discovery faces economic and scientific imperatives to deliver lead molecules rapidly and efficiently. Using traditional paradigms the molecular design, synthesis, and screening loops enforce a significant time delay leading to inefficient use of data in the iterative molecular design process. Here, we report the application of a flow technology platform integrating the key elements of structure-activity relationship (SAR) generation to the discovery of novel Abl kinase inhibitors. The platform utilizes flow chemistry for rapid in-line synthesis, automated purification, and analysis coupled with bioassay. The combination of activity prediction using Random-Forest regression with chemical space sampling algorithms allows the construction of an activity model that refines itself after every iteration of synthesis and biological result. Within just 21 compounds, the automated process identified a novel template and hinge binding motif with pIC50 > 8 against Abl kinase - both wild type and clinically relevant mutants. Integrated microfluidic synthesis and screening coupled with machine learning design have the potential to greatly reduce the time and cost of drug discovery within the hit-to-lead and lead optimization phases.
Desai, Bimbisar,Dixon, Karen,Farrant, Elizabeth,Feng, Qixing,Gibson, Karl R.,Van Hoorn, Willem P.,Mills, James,Morgan, Trevor,Parry, David M.,Ramjee, Manoj K.,Selway, Christopher N.,Tarver, Gary J.,Whitlock, Gavin,Wright, Adrian G.
supporting information
p. 3033 - 3047
(2013/05/22)

Cycloaddition-based formal C-H alkynylation of isoindoles leading to the synthesis of air-stable fluorescent 1,3-dialkynylisoindoles
Reaction of N-alkylisoindoles with (bromoethynyl)triisopropylsilane afforded 1,3-bis(triisopropylsilylethynyl) isoindoles in high yields. The formal C-H alkynylation proceeds under transition-metal-free conditions through [4 + 2] cycloaddition of the pyrrole ring of isoindole with bromoalkyne followed by ring-opening of the product.
Ohmura, Toshimichi,Kijima, Akihito,Komori, Yusuke,Suginome, Michinori
supporting information
p. 3510 - 3513
(2013/08/23)

Gold-catalyzed oxazoles synthesis and their relevant antiproliferative activities
Nine 5-aryl-2-methyloxazole derivatives were synthesized via gold-catalyzed alkyne oxidation. All of the compounds have been screened for their antiproliferative activities against MCF-7 cell (human breast carcinoma), A549 cell (human lung carcinoma) and
Wu, Chao,Liang, Zhi-Wu,Xu, Ying-Ying,He, Wei-Min,Xiang, Jian-Nan
p. 1064 - 1066
(2014/01/06)

OXAZOLIDINONES AS MODULATORS OF MGLUR5
The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands, agonists and partial agonists for the mGluR5 receptor and may be useful for the treatment of various disorders of the central nervous system.
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(2012/05/31)

Discovery of 5-(arenethynyl) hetero-monocyclic derivatives as potent inhibitors of BCR-ABL including the T315I gatekeeper mutant
Ponatinib (AP24534) was previously identified as a pan-BCR-ABL inhibitor that potently inhibits the T315I gatekeeper mutant, and has advanced into clinical development for the treatment of refractory or resistant CML. In this study, we explored a novel series of five and six membered monocycles as alternate hinge-binding templates to replace the 6,5-fused imidazopyridazine core of ponatinib. Like ponatinib, these monocycles are tethered to pendant toluanilides via an ethynyl linker. Several compounds in this series displayed excellent in vitro potency against both native BCR-ABL and the T315I mutant. Notably, a subset of inhibitors exhibited desirable PK and were orally active in a mouse model of T315I-driven CML.
Thomas, Mathew,Huang, Wei-Sheng,Wen, David,Zhu, Xiaotian,Wang, Yihan,Metcalf, Chester A.,Liu, Shuangying,Chen, Ingrid,Romero, Jan,Zou, Dong,Sundaramoorthi, Raji,Li, Feng,Qi, Jiwei,Cai, Lisi,Zhou, Tianjun,Commodore, Lois,Xu, Qihong,Keats, Jeff,Wang, Frank,Wardwell, Scott,Ning, Yaoyu,Snodgrass, Joseph T.,Broudy, Marc I.,Russian, Karin,Iuliucci, John,Rivera, Victor M.,Sawyer, Tomi K.,Dalgarno, David C.,Clackson, Tim,Shakespeare, William C.
scheme or table
p. 3743 - 3748
(2011/08/06)

A single-step synthesis of enynes: Pd-catalyzed arylalkynylation of aryl iodides, internal alkynes, and alkynylsilanes
"Chemical Equation Presented" An unprecedented single-step synthesis of enyne derivatives through Pd-catalyzed arylalkynylation of aryl iodides, internal alkynes, and alkynylsilanes is described.
Sakai, Norio,Komatsu, Ryosuke,Uchida, Naoki,Ikeda, Reiko,Konakahara, Takeo
supporting information; experimental part
p. 1300 - 1303
(2010/06/15)

Controlling hydrogen-bond preferences in bipyridines with competing binding sites
The design and synthesis of a family of supramolecular reagents (SRs) based on ethynyl-spaced substituted bipyridines are described, and their potential use as molecular 'hubs' for the predictable construction of binary and ternary co-crystals is explored. Each SR was synthesized in good yields through consecutive Pd-catalyzed Sonogashira cross-coupling reactions. Crystal structures of three binary co-crystals are presented with each structure clearly illustrating how accurate supramolecular assembly control can be achieved by increasing/decreasing the strength of the participating hydrogen-bond interactions.
Aaker?y, Christer B.,Schultheiss, Nate,Desper, John
scheme or table
p. 35 - 40
(2010/07/13)

Synthesis of 1-hetarylethylphosphonates
Previously unknown potentially biologically active diethyl 1-(pyridin-3-yl)-, 1-(quinolin-3-yl)-, and 1-(quinolin-6-yl)ethylphosphonates were synthesized by palladium-catalyzed reduction of the corresponding α,β-unsaturated precursors with ammonium formate. The reduction of diethyl 1-(quinolin-6-yl)ethenylphosphonate was accompanied by formation of diethyl 1-(1,2,3,4-tetrahydroquinolin-6-yl)ethylphosphonate as by-product.
Gulyukina,Beletskaya
scheme or table
p. 781 - 784
(2010/10/04)

The sequential Sonogashira-click reaction: A versatile route to 4-aryl-1,2,3-triazoles
Aryl halides can be easily transformed in a one-pot procedure into 4-aryl-1,2,3-triazoles with palladium/copper-catalyzed Sonogashira-click reaction sequence, using trimethylsilylacetylene as acetylene surrogate.
Loerincz, Krisztian,Kele, Peter,Novak, Zoltan
experimental part
p. 3527 - 3532
(2010/02/28)

Palladium-catalysed alkynylation of 2- or 3-bromopyridine
2- or 3-Alkynylpyridines were prepared using a palladium complex, in the absence of copper ions or amines. The mild procedure tolerated a range of 1-alkynes giving 2- or 3-alkynylpyridine in moderate to good yield.
Zhang, Weiwei,Cheng, Jiang,Huang, Zhengxu,Zhou, Qingqing,Chen, Xunmin,Qian, Jianzhu
p. 781 - 782
(2007/10/03)

Process for preparing alkynyl-substituted aromatic and heterocyclic compounds
Mono- and disubstituted aryl or heterocyclic acetylenes are produced by a process comprising reacting an aryl nitrile with an alkynylzinc compound, a bis-alkynylzinc compound, or an alkynylmagnesium compound, in the presence of a nickel/phosphine catalyst.
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(2010/02/12)

Triplet acetylenes as synthetic equivalents of 1,2-bicarbenes: Phantom n,π* state controls reactivity in triplet photocycloaddition
Diaryl acetylenes, in which one of the aryl groups is either a pyridine or a pyrazine, undergo efficient triplet state photocycloaddition to 1,4-cyclohexadiene with formation of 1,5-diaryl substituted tetracyclo[3.3.0. 02,8.04,6]octa
Zeidan, Tarek A.,Kovalenko, Serguei V.,Manoharan, Mariappan,Clark, Ronald J.,Ghiviriga, Ion,Alabugin, Igor V.
p. 4270 - 4285
(2007/10/03)

Alkynylation of benzonitriles via nickel catalyzed C-C bond activation
The scope of synthetically useful nickel catalyzed cross coupling reactions of benzonitriles has now been expanded to allow alkynylation. Thus, the cross coupling of benzonitriles with alkynylzinc reagents occurs readily in the presence of Ni/PMe3/s
Penney, Jonathan M.,Miller, Joseph A.
p. 4989 - 4992
(2007/10/03)

Efficient synthesis of a complete donor/acceptor bis(aryl)diyne family
A facile route to a family of bis(aryl)diynes containing both an electron donating pyridine ring and an electron accepting iodobenzene has been developed. The convergent synthesis involves the coupling of 2-, 3-, or 4-bromopyridine with TMS-acetylene, followed by deprotection to form the first half of the molecule. Similarly, 2-, 3-, or 4-iodoaniline was coupled to TMS-acetylene after protection of the amine group as a diethyltriazine. After conversion of the triazine to an iodine, deprotection of the acetylene and formation of the corresponding bromophenyl-acetylene, the two halves of the molecule were coupled under Cadiot-Chodkiewicz conditions. Nine new compounds were prepared, each of which was found to thermally polymerize from the melt. None of the compounds underwent photochemical polymerization in the solid-state.
Holmes, Brian T.,Pennington, William T.,Hanks, Timothy W.
p. 2447 - 2461
(2007/10/03)

Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidase.
The synthesis of a novel series of 3-phenylprop-2-ynylamines as selective mammalian squalene epoxidase inhibitors is described. Structure activity relationship studies led to the discovery of compound 19, 1-[3-(3,5-dichlorophenyl)-prop-2-ynyl]-3- methylpiperidine hydrochloride with an IC50 of 2.8 +/- 0.6 microM against rat liver squalene epoxidase. Against 23 strains of fungal squalene epoxidase compound 19 was found to be inactive.
Musso, David L,Clarke, Morris J,Kelley, James L,Boswell, G Evan,Chen, Grace
p. 498 - 506
(2007/10/03)

Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates
Sodium tetraalkynylaluminates (1-4), prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both hom
Gelman, Dmitri,Tsvelikhovsky, Dmitry,Molander, Gary A.,Blum, Jochanan
p. 6287 - 6290
(2007/10/03)

Syntheses and characterization of 1,1'-bis(3-pyridylethynyl)ferrocene and 1,1'-bis(4-pyridylethynyl)ferrocene
Two novel disubstituted ferrocene, 1,1'-bis(3-pyridylethynyl)ferrocene 1 and 1,1'-bis(4-pyridylethynyl)ferrocene 2, were synthesized and fully characterized by elemental analysis, 1H NMR 13C NMR IR, and X-ray crystallography. Compound 1crystallizes in monoclinic, space group Cc, a=17.26?, b=9.77?, c=10.85?, β=105.45; R1 =0.0399, wR2=0.1077, GooF=1.023. The two arms of the ferrocene are parallel, which will play an important role both in the coordination chemistry and electronic communiculion of the ferrocene.
Lindner, Ekkehard,Zong, Ruifa,Eichele, Klaus
p. 219 - 222
(2007/10/03)

Rapid homogeneous-phase sonogashira coupling reactions using controlled microwave heating
A microwave-enhanced, rapid and efficient homogeneous-phase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides, bromides, triflates, and aryl chloride, as well as pyridine and thiophene derivatives with t
Erdelyi,Gogoll
p. 4165 - 4169
(2007/10/03)

A Facile Synthesis of Ethynyl-Substituted Six-Membered N-Heteroaromatic Compounds
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Sakamoto, Takao,Shiraiwa, Masafumi,Kondo, Yoshinori,Yamanaka, Hiroshi
p. 312 - 314
(2007/10/02)