- Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants
-
2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).
- Jeremias, Noah,Mohr, Lisa-Marie,Bach, Thorsten
-
supporting information
p. 5674 - 5678
(2021/08/03)
-
- One-Pot Copper-Catalyzed Three-Component Reaction of Sulfonyl Azides, Alkynes, and Allylamines to Access 2,3-Dihydro-1 H-imi-dazo[1,2-a]indoles
-
A copper-catalyzed multicomponent reaction of sulfonyl azides, alkynes, and allylamines affording 2,3-dihydro-1 H-imidazo-[1,2-a]indoles in moderate yields is reported. Four C-N bonds are constructed- by way of azide-alkyne cycloaddition (CuAAC) and double Ullmann-type coupling reactions in a one-pot process.
- Jin, Hongwei,Liu, Daohong,Liu, Yunkui,Zhou, Bingwei
-
supporting information
p. 1417 - 1424
(2020/04/27)
-
- Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes
-
The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionaliz
- Liang, Hao,He, Xiaobo,Zhang, Yaqi,Chen, Bin,Ouyang, Jia-Sheng,Li, Yongsu,Pan, Bendu,Subba Reddy, Chitreddy V.,Chan, Wesley Ting Kwok,Qiu, Liqin
-
supporting information
p. 11429 - 11432
(2020/10/12)
-
- Design, Synthesis, and in vitro Evaluation of P2X7 Antagonists
-
The P2X7 receptor is a promising target for the treatment of various diseases due to its significant role in inflammation and immune cell signaling. This work describes the design, synthesis, and in vitro evaluation of a series of novel derivatives bearing diverse scaffolds as potent P2X7 antagonists. Our approach was based on structural modifications of reported (adamantan-1-yl)methylbenzamides able to inhibit the receptor activation. The adamantane moieties and the amide bond were replaced, and the replacements were evaluated by a ligand-based pharmacophore model. The antagonistic potency of the synthesized analogues was assessed by two-electrode voltage clamp experiments, using Xenopus laevis oocytes that express the human P2X7 receptor. SAR studies suggested that the replacement of the adamantane ring by an aryl-cyclohexyl moiety afforded the most potent antagonists against the activation of the P2X7 cation channel, with analogue 2-chloro-N-[1-(3-(nitrooxymethyl)phenyl)cyclohexyl)methyl]benzamide (56) exhibiting the best potency with an IC50 value of 0.39 μΜ.
- Durner, Anna,Koufaki, Maria,Kritsi, Eftichia,Nicke, Annette,Papakostas, Alexios,T. Pournara, Dimitra,Zoumpoulakis, Panagiotis
-
p. 2530 - 2543
(2020/10/19)
-
- Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes
-
The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.
- Cloutier, Mélissa,Roudias, Majdouline,Paquin, Jean-Fran?ois
-
supporting information
p. 3866 - 3870
(2019/05/24)
-
- SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes
-
Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).
- Zha, Gao-Feng,Fang, Wan-Yin,Li, You-Gui,Leng, Jing,Chen, Xing,Qin, Hua-Li
-
supporting information
p. 17666 - 17673
(2019/01/04)
-
- Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5-hydroxybenzofuran derivatives
-
A palladium-catalyzed benzoquinone C-H functionalization/ cyclization strategy with terminal alkynes was employed for the synthesis of some biologically relevant 2, 3-disubstituted 5-hydroxybenzofuran derivatives. The benzoquinone acts as a reactant as well as an oxidant. During the process, an additional alkyne functionality can be introduced at the C3 position of the benzofuran. Base, ligand, and external oxidant are not required in this protocol.
- Ichake, Sachin S.,Konala, Ashok,Kavala, Veerababurao,Kuo, Chun-Wei,Yao, Ching-Fa
-
supporting information
p. 54 - 57
(2017/11/28)
-
- Efficient synthesis of N-arylsulfonyl-1,2,3-triazoles from 1,1-dibromo-2-arylethylenes
-
N-arylsulfonyl-1,2,3-triazoles were synthesized from 1,1-dibromo-2-arylethylenes via a one-pot reaction involving the Cs2CO3-mediated dehydrobromination process of the dibromoalkenes to produce alkynes followed by the Cu(I)-catalyzed Huisgen cycloaddition of the alkyne intermediates with tosyl azide.
- Xu, Wenjing,Zhang, Wensheng,Zhang, Fei
-
p. 165 - 167
(2016/07/06)
-
- Synthesis of 1-arylsulfonyl-1,2,3-triazoles from (Z)-arylvinyl bromides by sequential elimination–cycloaddition reaction
-
[Figure not available: see fulltext.]Efficient synthesis of 1-arylsulfonyl-1,2,3-triazoles from easily available (Z)-arylvinyl bromides is described. The sequential reaction involves elimination of HBr from (Z)-arylvinyl bromides promoted by KOH and copper-catalyzed (3+2) cycloaddition reaction between the alkyne intermediates and sulfonyl azides.
- Zhang, Wensheng,Xu, Wenjing
-
p. 192 - 195
(2016/07/28)
-
- An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin
-
An efficient method of preparing various terminal alkynes from 1,1-dibromo-1-alkenes by using TBAF (tetra-n-butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.
- Liu, Shihui,Chen, Xiaobei,Hu, Yanwei,Yuan, Laiqi,Chen, Shaohua,Wu, Ping,Wang, Wei,Zhang, Shilei,Zhang, Wei
-
p. 553 - 560
(2015/03/05)
-
- Visible-Light-Promoted Vinylation of Tetrahydrofuran with Alkynes through Direct C-H Bond Functionalization
-
(Chemical Equation Presented) Mild and direct C-H bond functionalizations and vinylations of tetrahydrofuran with alkynes have been accomplished through visible light photocatalysis, yielding a range of vinyl tetrahydrofurans under the synergistic actions of organic dye-type photocatalyst eosin Y, tert-butyl hydroperoxide (t-BuOOH), and a 45 W household lightbulb. A significant kinetic isotope effect (KIE) was recorded, which helps shed light on the mechanistic course.
- Li, Jing,Zhang, Jing,Tan, Haibo,Wang, David Zhigang
-
supporting information
p. 2522 - 2525
(2015/05/27)
-
- "quick and click" assembly of functionalised indole rings via metal-promoted cyclative tandem reactions
-
An efficient and convenient synthesis of a variety of decorated indoles using a three-component tandem metal-catalysed process is described. We propose here a new "synthetic kit" that allows for the "quick and click" assembly of indole rings using readily available, and inexpensive starting materials under environmentally friendly reaction conditions. This journal is
- Capitta, Francesca,De Luca, Lidia,Porcheddu, Andrea
-
p. 59297 - 59301
(2015/02/19)
-
- Regio- and stereoselective dimerization of arylacetylenes and optical and electrochemical studies of (E)-1,3-enynes
-
The N-heterocyclic carbene palladium complex (SIPr)Pd(cinnamyl)Cl [SIPr=N,N'-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene) promotes regio- and stereospecific dimerization of a variety of arylalkynes to give (E)-1,3-enynes in good to excellent yields. An efficient and practical procedure for their synthesis was developed using a biphasic aqueous alkali/heptane system. Optical and electronic properties of (E)-1,3-enynes are highly tunable. Depending on the nature of the substituents, HOMO energies vary in the range 5.3-6.0eV. (E)-1,3-Enynes can exhibit intense photoluminescence in the spectral region 350-500nm.
- Morozov, Oleg S.,Asachenko, Andrey F.,Antonov, Denis V.,Kochurov, Vitaly S.,Paraschuk, Dmitry Yu.,Nechaev, Mikhail S.
-
supporting information
p. 2671 - 2678
(2014/09/29)
-
- 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)
-
- Cs2CO3-mediated synthesis of terminal alkynes from 1,1-dibromo-1-alkenes
-
An unprecedented route to prepare terminal alkynes from 1,1-dibromo-1-alkenes mediated by Cs2CO3 was proven. 1,1-Dibromo-1-alkenes bearing various functional groups were efficiently converted to corresponding terminal alkynes in moderate to excellent yields.
- Zhao, Ming,Kuang, Chunxiang,Yang, Qing,Cheng, Xuezhi
-
scheme or table
p. 992 - 994
(2011/03/22)
-
- Convenient synthesis of terminal alkynes from anti-3-aryl-2,3- dibromopropanoic acids using a K2CO3/DMSO system
-
A convenient, efficient, and generally applicable method was developed for the synthesis of terminal alkynes from anti-3-aryl-2,3-dibromopropanoic acids in the presence of DMSO and K2CO3.
- Cheng, Xuezhi,Jia, Jun,Kuang, Chunxiang
-
experimental part
p. 2350 - 2354
(2012/02/03)
-
- Synthesis and antiplasmodial activity of new indolone N-Oxide derivatives
-
A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), aswell as for cytotoxic concentration (CC50) on MCF7 and KB human tumor cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day. 2009 American Chemical Society.
- Nepveu, Fran?oise,Kim, Sothea,Boyer, Jeremie,Chatriant, Olivier,Ibrahim, Hany,Reybier, Karine,Monje, Marie-Carmen,Chevalley, Severine,Perio, Pierre,Lajoie, Barbora H.,Bouajila, Jalloul,Deharo, Eric,Sauvain, Michel,Tahar, Rachida,Basco, Leonardo,Pantaleo, Antonella,Turini, Francesco,Arese, Paolo,Valentin, Alexis,Thompson, Eloise,Vivas, Livia,Petit, Serge,Nallet, Jean-Pierre
-
experimental part
p. 699 - 714
(2010/07/09)
-
- 7H-PYRIDO[3,4-D]PYRIMIDIN-8-ONES, THEIR MANUFACTURE AND USE AS PROTEIN KINASE INHIBITORS
-
Objects of the present invention are the compounds of formula (I) their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates, the preparation of the above compounds, medicaments containing them and their manufacture, as we
- -
-
Page/Page column 32-33
(2008/06/13)
-
- One-step synthesis of aromatic terminal alkynes from their corresponding ketones under microwave irradiation
-
One-step microwave-assisted synthesis of phenylacetylenes 2a-j from the corresponding ketones 1a-j in the presence of a new reagent, PCl 5 -pyridine, is described. The reaction is carried out under a simple operational and experimental procedure, avoiding the use of the complicated and harsh multistep reaction. Copyright Taylor & Francis Group, LLC.
- Ghaffarzadeh, Mohammad,Bolourtchian, Mohammad,Fard, Zohreh,Halvagar, Mohammad,Mohsenzadeh, Farshid
-
p. 1973 - 1981
(2007/10/03)
-
- Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction
-
(Z)-1-Bromo-1-alkenes were stereoselectively prepared in high yields in a short reaction time by microwave irradiation of the corresponding anti-2,3-dibromoalkanoic acids in a Et3N/DMF system. A one-pot synthesis of terminal alkynes and enynes from 2,3-dibromoalkanoic acids were also developed by microwave-induced reaction.
- Kuang, Chunxiang,Yang, Qing,Senboku, Hisanori,Tokuda, Masao
-
p. 4043 - 4052
(2007/10/03)
-
- A one-pot synthesis of terminal alkynes from anti-3-aryl-2,3- dibromopropanoic acids under microwave irradiation
-
A facile one-pot synthesis of terminal alkynes was achieved by microwave irradiation of a mixture of anti-3-aryl-2,3-dibromopropanoic acids, Et 3N and DMF and subsequent irradiation in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). This method requires short reaction time (1-2 min) and gives terminal alkynes in high yields. Copyright
- Kuang, Chunxiang,Senboku, Hisanori,Tokuda, Masao
-
-
- Microwave-assisted in situ deprotection and ω-methoxylation of TMS-protected aryl alkynes
-
Using microwave technology, rapid ω-methoxylation of aryl alkynes is possible.
- Wettergren, Jenny,Minidis, Alexander B. E.
-
p. 7611 - 7612
(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)
-
- Formation and decomposition of chloroaromatic compounds in chlorine-containing benzene/oxygen flames
-
Premixed chlorine-containing, fuel-rich, low-pressure benzene/oxygen flames were analysed for the formation of (oxygenated) chloroaromatic compounds and their radicals by means of the condensation/radical-scavenging method (Hausmann, M., Homann, K.-H., 1995. Ber. Busenges. Phys. Chem. 99, 853-862). Several chlorinated organic compounds (methyl chloride, t-butyl chloride, chlorobenzene, chloroform) were used as additives within a maximum concentration of 10% of total fuel. Product identification and quantification were performed by GC/MS. The extent of formation of chloroaromatic compounds in these flames was largest in the cases of chlorobenzene and chloroform as additives. For chlorobenzene, 12 different chloroaromatics could be analysed in between C7H7Cl and C12H9Cl. Their formation is mainly due to conversion of initial chlorobenzene into substituted or oxidised derivatives, or growth products. Additional chlorination of aromatics is shown to be of minor importance in chlorobenzene-containing flames. Three isomeric (o/m/p) scavenging products could be identified for the chlorophenyl radical. In the chloroform case, 15 chloroaromatics could be analysed in between C6H5Cl and C14H9Cl. The weak C-Cl bond in chloroform is responsible for the high extent of chloroaromatics formation, either by Cl abstraction from the additive or by chlorination reactions via Cl radicals. Additionally, specific pathways to (di)chloroaromatics and chlorinated fulvene-type structures are outlined via CHCl2 and CCl2 radicals.
- Burfeindt,Homann
-
p. 439 - 447
(2007/10/03)
-
- An Efficient and General Procedure for the Cross-Coupling of Trimethylsilylacetylene and Vinylic, Aromatic or Heteroaromatic Bromides.
-
Coupling reactions of trimethylsilylacetylene and vinylic, aromatic or heteroaromatic bromides can be carried out in very short time and with excellent yield using piperidine as a solvent and very small amounts of tetrakis(triphenylphosphine)palladium and
- Brandsma, L.,Heuvel, H.G.M. van den,Verkruijsse, H.D.
-
p. 1889 - 1892
(2007/10/02)
-
- SYNTHESIS OF o-HALOGENOPHENYLACETYLENES VIA THE DIANION OF PHENYLACETYLENE
-
The o-halogenophenylacetylenes o-iodophenylacetylene, o-bromophenylacetylene and o-chlorophenylacetylene can be prepared by regiospecific reaction of iodine, bromine and hexachloroethane respectively with the dianion of phenylacetylene.
- Hommes, H,Verkruijsse, H. D.,Brandsma, L.
-
p. 2495 - 2496
(2007/10/02)
-
- Choix des methodes pour la synthese univoque de carbures acetyleniques. Troisieme partie : Arylacetylenes et aryl-1 alcynes-1
-
The range of applicability of six syntheses of pure alkynes with one aryl group has been defined; a short review of other possible procedures is included.We have specified the best method to obtain selectively the alkynes Ar-CCH and Ar-CC-R, according to the nature of the substituents of the aryl group and according to the developed structure of the R group.It is thus possible to recommend with the largest probability of success the method to obtain, in homogenous series, alkynes corresponding to still more complicated structures.
- Mesnard, Danielle,Bernadou, Francoise,Miginiac, Leone
-
p. 3216 - 3245
(2007/10/02)
-