- Synthesis of chromeno[2,3-c]pyrrol-9(2H)-ones by domino Michael-Claisen-SNAr reactions of amino acid esters with 2-chlorophenylpropynones
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The domino reaction of amino acid esters with 2-chlorophenylpropynones, readily available by Sonogashira reactions of 2-chlorobenzoylacetylenes, afforded novel chromeno[2,3-c]pyrrol-9(2H)-ones. The domino reaction involves three steps, i.e. Michael, Clais
- Dang, Tuan T.,Ehlers, Peter,Langer, Peter,Miliutina, Mariia,Nguyen Tien, Tuan Anh,Radolko, Jan,Thom, Richard
-
-
- Elemental chalcogen (Se, S) in PEG-400 to the synthesis of seleno- And thioflavones from 2-chlorophenyl ethynyl ketone and nucleophilic species of chalcogen
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An alternative green method was developed for the synthesis of thio- and selenoflavones by the ring closure of 2-chlorophenyl ethynyl ketone with NaHY (Y = S, Se). These nucleophilic chalcogen species were generated in situ using NaBH4 to reduc
- Barcellos, Angelita M.,Barcellos, Thiago,Bartz, Ricardo H.,Jacob, Raquel G.,Nobre, Patrick C.,Peglow, Thiago J.,Perin, Gelson,Silva, Márcio S.
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p. 1541 - 1551
(2021/07/06)
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- Synthesis of 2-isoxazolyl-2,3-dihydrobenzofuransviapalladium-catalyzed cascade cyclization of alkenyl ethers
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A novel palladium-catalyzed cascade cyclization reaction of alkenyl ethers with alkynyl oxime ethers for the construction of poly-heterocyclic scaffolds has been developed, in which the electron-rich alkene moiety functions as a three-atom unit, simultaneously dealing well with the coordination and regioselectivity of electron-rich olefins under metal catalysis. The strategy features excellent regio- and chemoselectivities as well as good functional group tolerance. Moreover, the newly formed 2-isoxazolyl-2,3-dihydrobenzofuran products can be further transformed to diverse complex heterocycles, demonstrating their potential applications in organic synthesis and medicinal chemistry.
- Zhou, Fei,Li, Can,Li, Meng,Jin, Yangbin,Jiang, Huanfeng,Zhang, Yingjun,Wu, Wanqing
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supporting information
p. 4799 - 4802
(2021/05/25)
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- Methylation Alkynylation of Terminal Alkenes via 1,2-Alkynyl Migration Using Dicumyl Peroxide as the Methyl Source
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The metal-free oxidative alkene methylation/alkynylation of 1,4-enyn-3-ols with an organic peroxide as the methyl source has been developed, which provides straightforward and practical access to the challenging quaternary-carbon-containing but-3-yn-1-one
- Qin, Yi-Qun,Chen, De,Liu, Liang,Zhang, Jia-Jia,Peng, Xin-Ju,Luo, Yong-Yue,Deng, Wei,Xiang, Jiannan
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p. 4700 - 4708
(2021/08/31)
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- Selective Insertion of Alkynes into C-C σ Bonds of Indolin-2-ones: Transition-Metal-Free Ring Expansion Reactions to Seven-Membered-Ring Benzolactams or Chromone Derivatives
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An unprecedented ring expansion reaction of indolin-2-ones with alkynyl ketones under transition-metal-free conditions has been developed. Base-promoted selective cleavage of a C-C σ bond of the amide is the key in this process, which provides a straightf
- Wang, Mengdan,Yang, Yajie,Song, Bo,Yin, Liqiang,Yan, Shuhui,Li, Yanzhong
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p. 155 - 159
(2020/01/03)
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- Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F
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An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.
- Mehta, Goverdhan,Nerella, Sharanya,Pabbaraja, Srihari,Singh, Shweta
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- Synthesis and Characterization of Ag@g?C3N4 and Its Photocatalytic Evolution in Visible Light Driven Synthesis Of Ynone
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The primary aim of this work is to synthesize photocatalyst to promote the synthesis of ynones. In this context, we synthesized AgNPs@g?C3N4 nanocomposite. The nanocomposite was characterized by using SEM, HR-TEM, XRD, EDS, ICP-AES,
- Patel, Sunil B.,Vasava, Dilip V.
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p. 631 - 641
(2019/12/03)
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- Base-Promoted Michael Addition/Smiles Rearrangement/ N-Arylation Cascade: One-Step Synthesis of 1,2,3-Trisubstituted 4-Quinolones from Ynones and Sulfonamides
-
A general, practical, and environmentally friendly protocol to synthesize 1,2,3-trisubstituted 4-quinolones from readily available ynones and sulfonamides was developed. The construction of one C?C bond and two C?N bonds via cleavage of one N?S, one C?S,
- Liu, Jing,Ba, Dan,Lv, Weiwei,Chen, Yanhui,Zhao, Zemin,Cheng, Guolin
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supporting information
p. 213 - 223
(2019/12/11)
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- Synthesis of 3-(2-quinolyl) chromones from ynones and quinoline: N -oxides via tandem reactions under transition metal- And additive-free conditions
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A novel method for the synthesis of 3-(2-quinolyl) chromones through a tandem [3+2] cycloaddition/ring-opening/O-arylation from ynones and quinoline N-oxides has been developed. This protocol proceeds under transition metal- and additive-free conditions a
- Liu, Jing,Ba, Dan,Chen, Yanhui,Wen, Si,Cheng, Guolin
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supporting information
p. 4078 - 4081
(2020/04/20)
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- Palladium-Catalyzed Oxidative C≡C Triple Bond Cleavage of 2-Alkynyl Carbonyl Compounds Toward 1,2-Dicarbonyl Compounds?
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A new, general palladium-catalyzed oxidative strategy for the cleavage of the C≡C triple bond is presented. By employing PdCl2, CuBr2, TEMPO and air as the catalytic system and H2O as the carbonyl oxygen atom source, a wide range of 2-alkynyl carbonyl compounds, including 1,3-disubstituted prop-2-yn-1-ones, propiolamides and propiolates, lost an alkynyl carbon to access various 1,2-dicarbonyl compounds, e.g., 1,2-diones, 2-keto amides and 2-keto esters, through Wacker oxidation, intramolecular cyclization and C—C bond cleavage cascades.
- Hu, Ming,Li, Jin-Heng,Luo, Mu-Jia,Zhou, Ming-Bo
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supporting information
p. 553 - 558
(2020/04/20)
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- Palladium-catalyzed carbonylative Sonogashira cross-coupling for the synthesis of alkynones with formic acid as the CO source
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Abstract: A practical and efficient palladium-catalyzed carbonylative Sonogashira cross-coupling reaction for the synthesis of alkynones from aryl iodides, alkynes, and formic acid as the CO source has been described. Under the assistance of PPh3/I2, formic acid can be used as the CO source for synthesis of alkynones in moderate–good yields. Furthermore, it is also successfully applied for the modification of natural products, such as vindoline and tabersonin, to obtain the corresponding products.
- Lyu, Xue,Sun, Guanglong,Zhou, Yang,Wang, Yingying,Lei, Min,Wu, Wanying,Guo, Dean
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p. 309 - 315
(2019/01/21)
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- Synthesis of (: Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid
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A convenient and broadly applicable method for the hydrohalogenation of ynones is described, by the combination of halotrimethylsilanes and tetrafluoroboric acid. Practically, one equivalent of HX (Br?nsted acid) and BF3 (Lewis acid) is smoothly generated, which activates the carbonyl compounds. Through this protocol, 42 examples of (Z)-β-halovinyl carbonyl compounds (Cl, Br and I) were obtained, in good yields and high stereoselectivity having 2-MeTHF as a solvent.
- Da Silva, Vitor A. F.,Da Silva, Gustavo P.,Matsuo, Bianca T.,Ali, Akbar,Davis, Rebecca L.,Zukerman-Schpector, Julio,Corrêa, Arlene G.,Paix?o, Márcio W.
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supporting information
p. 519 - 526
(2019/01/24)
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- Photocatalytic Annulation-Alkynyl Migration Strategy for Multiple Functionalization of Dual Unactivated Alkenes
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A novel photoredox catalysis for multiple functionalization of two different types of unactivated alkenes in a single operation was reported through a conceptually new mode of annulation-alkynyl migration. A wide array of cyclopentane carboxylates were sy
- Zhao, Qi,Hao, Wen-Juan,Shi, Hao-Nan,Xu, Ting,Tu, Shu-Jiang,Jiang, Bo
-
supporting information
p. 9784 - 9789
(2019/12/24)
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- Metal-Free Promoted CF2/CF3-Difunctionalization of Unactivated Alkenes
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An operationally simple radical difluoroalkylation/trifluoromethylation and alkynylation of unactivated alkenes under mild conditions has been developed. Through this protocol, a series of CF2/CF3- substituted linear alkynyl ketones
- Li, Ming,Zhu, Xin-Yu,Qiu, Yi-Feng,Han, Ya-Ping,Xia, Yu,Wang, Cui-Tian,Li, Xue-Song,Wei, Wan-Xu,Liang, Yong-Min
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supporting information
p. 2945 - 2950
(2019/04/27)
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- Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
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Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).
- Meng, Mengting,Wang, Guofang,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
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p. 1218 - 1231
(2018/02/16)
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- Nitromethane as a Carbanion Source for Domino Benzoannulation with Ynones: One-Pot Synthesis of Polyfunctional Naphthalenes and a Total Synthesis of Macarpine
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A one-pot, transition-metal-free, domino Michael/SNAr protocol of general applicability has been devised for the regioselective synthesis of polyfunctional naphthalenes by employing nitromethane and ortho-haloaryl ynones. Utilization of nitromethane as a one carbon carbanion source that is incorporated into a variety of ynones, ends up as an aromatic nitro substituent. The application of this domino process towards a total synthesis of the polycyclic alkaloid macarpine demonstrate for the efficacy of this methodology. The conceptually simple approach to affect regioselective, multifunctional benzoannulation of ynones displays wide substrate scope and functional-group tolerance and has been implemented with substituted nitromethanes, as well as with alicyclic o-haloynones.
- Singh, Shweta,Samineni, Ramesh,Pabbaraja, Srihari,Mehta, Goverdhan
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p. 16847 - 16851
(2018/11/27)
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- Combining Electronic and Steric Effects to Generate Hindered Propargylic Alcohols in High Enantiomeric Excess
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Tethered ruthenium-TsDPEN complexes have been applied to the catalysis of the asymmetric transfer hydrogenation of a range of aryl/acetylenic ketones. The introduction of an ortho- substituent to the aryl ring of the substrate results in a reversal of the
- Vyas, Vijyesh K.,Knighton, Richard C.,Bhanage, Bhalchandra M.,Wills, Martin
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p. 975 - 978
(2018/02/23)
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- Merging " Anti-Baldwin" 3- Exo-Dig Cyclization with 1,2-Alkynyl Migration for Radical Alkylalkynylation of Unactivated Olefins
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A new combination of "anti-Baldwin" 3-exo-dig cyclization with 1,2-alkynyl migration of 1,4-enynes with simple cycloalkanes was established, enabling C-C breaking and reconstruction to access a wide range of α-alkynyl ketones with generally good yields by
- Zhao, Qi,Ji, Xiao-Shuang,Gao, Yi-Yun,Hao, Wen-Juan,Zhang, Ke-Ying,Tu, Shu-Jiang,Jiang, Bo
-
supporting information
p. 3596 - 3600
(2018/06/26)
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- Consecutive Alkynylation-Michael Addition-Cyclocondensation (AMAC) Multicomponent Syntheses of α-Pyrones and α-Pyridones
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A novel consecutive three-component synthesis of α-pyrones is based upon an alkynylation-Michael addition-cyclocondensation (AMAC) sequence, starting from (hetero)aroyl chloride and terminal alkyne to furnish the alkynone which reacts with malonates to gi
- Breuer, Natascha,Müller, Thomas J. J.
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p. 2741 - 2752
(2018/06/08)
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- An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources
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An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.
- Chen, Pei,Zhang, Qian-Qian,Guo, Jia,Chen, Lu-Lu,Wang, Yan-Bo,Zhang, Xiao
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p. 6958 - 6966
(2018/10/02)
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- A Convenient and Efficient Palladium-Catalyzed Carbonylative Sonogashira Transformation with Formic Acid as the CO Source
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A practical, convenient, and efficient palladium-catalyzed carbonylative Sonogashira reaction of aryl iodides was developed. With formic acid as the CO source and dicyclohexylcarbodiimide as the activator, various alkynones were produced in good to excell
- Peng, Jin-Bao,Wu, Fu-Peng,Li, Chong-Liang,Qi, Xinxin,Wu, Xiao-Feng
-
supporting information
p. 1434 - 1437
(2017/04/01)
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- Base-mediated insertion reaction of alkynes into carbon-carbon σ-bonds of ethanones: synthesis of hydroxydienone and chromone derivatives
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Transition-metal free insertions of alkynes into carbon-carbon σ-bonds of ethanones have been reported. These tandem reactions offer an efficient synthesis of hydroxydienones and multi-substituted chromones. This is the first example of base-promoted insertion reactions of isolated carbon-carbon triple bonds into carbon-carbon σ-bonds with active methylene compounds bearing only one electron-withdrawing group.
- Zhang, Fangfang,Yao, Qiyi,Yuan, Yang,Xu, Murong,Kong, Lingkai,Li, Yanzhong
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p. 2497 - 2500
(2017/04/03)
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- Base-Promoted Tandem Reaction towards Conjugated Dienone or Chromone Derivatives with a Cyano Group: Insertion of Alkynes into C–C σ-Bonds of 3-Oxopropanenitriles
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Base-promoted insertion reactions of alkynes into the C–C σ-bonds of α-cyano ketones were established to construct highly functionalized conjugated olefins or chromone derivatives via transition metal-free tandem reactions. These reactions are initialized through the nucleophilic attack of α-cyano ketones to alkynones followed by intramolecular nucleophilic addition/ring-opening to furnish the cyano-containing alkenes. In the cases of alkynones bearing an ortho-halide-substituted aryl ring, a further C–O bond coupling reaction occurs to afford chromone derivatives in good to high yields. Various alkynones bearing alkyl or aryl substituents were compatible in the reaction. This reaction has the potential to become a general synthetic protocol for the preparation of cyano-substituted olefins and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups. (Figure presented.).
- Yao, Qiyi,Kong, Lingkai,Zhang, Fangfang,Tao, Xianghua,Li, Yanzhong
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p. 3079 - 3084
(2017/09/13)
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- A facile and efficient method for the synthesis of alkynone by carbonylative Sonogashira coupling using CHCl3 as the CO source
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A facile and efficient method for the synthesis of alkynones by a Pd-catalyzed carbonylative Sonogashira coupling reaction starting from aryl iodide, terminal alkyne and chloroform (CHCl3) as the CO source is described. This procedure proves th
- Sun, Guanglong,Lei, Min,Hu, Lihong
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p. 28442 - 28446
(2016/04/09)
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- Base-Promoted Tandem Reaction Involving Insertion into Carbon–Carbon σ-Bonds: Synthesis of Xanthone and Chromone Derivatives
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Tandem reactions using base-promoted processes have been developed for the synthesis of xanthone and chromone derivatives. The first examples of base-promoted insertion reactions of isolated carbon–carbon triple bonds into carbon–carbon σ-bonds have been reported. Using these approaches, polycyclic structures can be prepared. This reaction has the potential to become a general synthetic protocol for the preparation of multi-substituted xanthones and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups.
- Cheng, Xingcan,Zhou, Yuanyuan,Zhang, Fangfang,Zhu, Kai,Liu, Yuanyuan,Li, Yanzhong
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supporting information
p. 12655 - 12659
(2016/08/30)
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- Insertion of Isolated Alkynes into Carbon–Carbon σ-Bonds of Unstrained Cyclic β-Ketoesters via Transition-Metal-Free Tandem Reactions: Synthesis of Medium-Sized Ring Compounds
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The transition-metal-free insertion of isolated alkynes into carbon–carbon σ-bonds of unstrained cyclic β-dicarbonyl compounds has been reported. These tandem reactions offer an efficient synthesis of medium-sized ring or fused-ring compounds through ring expansion. The methodology has the potential to be widely used throughout organic synthesis due to the easily accessible starting materials and mild reaction conditions.
- Zhou, Yuanyuan,Tao, Xianghua,Yao, Qiyi,Zhao, Yulei,Li, Yanzhong
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p. 17936 - 17939
(2016/12/16)
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- Oxidative Coupling of Terminal Alkynes with Aldehydes Leading to Alkynyl Ketones by Using Indium(III) Bromide
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An indium(III)-promoted direct acylation of terminal alkynes using aldehydes leading to ynones was developed. In contrast to the previous addition reactions of alkynes to aldehydes, which provide propargylic alcohols, the oxidative coupling proceeded exclusively to afford alkynyl ketones. The products were likely generated through an Oppenauer oxidation of the indium propargylic alkoxide species by excess amounts of aldehydes.
- Ogiwara, Yohei,Kubota, Masahito,Kurogi, Kotaro,Konakahara, Takeo,Sakai, Norio
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supporting information
p. 18598 - 18600
(2016/01/25)
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- Sunlight-Driven Decarboxylative Alkynylation of α-Keto Acids with Bromoacetylenes by Hypervalent Iodine Reagent Catalysis: A Facile Approach to Ynones
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A novel and practical decarboxylative alkynylation of α-keto acids with bromoacetylenes is catalyzed by hypervalent iodine(III) reagents when irradiation by sunlight at room temperature. The product ynones are generated in good yields. Experiments show that results obtained with blue light (λ=450-455 nm) are comparable to those obtained when using sunlight. Mechanistic studies demonstrate that the sunlight-driven decarboxylation undergoes a radical process.
- Tan, Hui,Li, Hongji,Ji, Wangqin,Wang, Lei
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supporting information
p. 8374 - 8377
(2015/11/27)
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- Palladium-Catalyzed One-Pot Carbonylative Sonogashira Reaction Employing Formic acid as the CO Source
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A convenient palladium-catalyzed carbonylative coupling of aryl iodides and terminal alkynes with formic acid as the CO precursor has been developed. A variety of alkynones were obtained in good yields in a one-pot manner for the first time. CO Confidenti
- Qi, Xinxin,Jiang, Li-Bing,Li, Chong-Liang,Li, Rui,Wu, Xiao-Feng
-
supporting information
p. 1870 - 1873
(2015/09/07)
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- Synthesis and biological evaluation of acetylenic chalcones as novel anti-inflammatory agents
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37 acetylenic chalcones were designed, synthesized by the Pd/Cu catalyzed Sonogashira coupling reaction, and evaluated for anti-inflammatory activities. A majority of these compounds showed remarkable inhibitions of the expression of inflammatory cytokine
- Zhao, Chengguang,Feng, Jianpeng,Zuo, Mingming,Zhang, Ying,Zhao, Jianfeng,Xu, Shanmei,Zheng, Suqing,Zhang, Yali,Tang, Qinqin,Lu, Zhongqiu,Liang, Guang,Zhou, Jianmin
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p. 567 - 572
(2015/08/18)
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- Dual-immobilized copper catalyst: Carbon nitride-supported copper nanoparticles catalyzed oxidation of propargylic alcohols
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Copper nanoparticles were supported and modified by carbon nitride, which was utilized as support and might work as a kind of immobilized N-donor ligand. The modified nanoparticle catalyst was evaluated with the oxidation of propargylic alcohols and showed highly catalytic efficiency as well as significant ligand or support effect in the reaction. The dual-immobilized nanoparticle catalyst could be recycled for 3 times at least without an obvious decrease in catalytic activities.
- Lv, Wei,Tian, Jing,Deng, Nan,Wang, Yan,Zhu, Xiaoshu,Yao, Xiaoquan
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supporting information
p. 1312 - 1316
(2015/03/04)
-
- Sequential palladium catalyzed coupling-cyclocondensation-coupling (C3) four-component synthesis of intensively blue luminescent biarylsubstituted pyrazoles
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1-, 3-, and 5-Biarylsubstituted pyrazoles can be efficiently prepared by a microwave-assisted consecutive four-component synthesis based upon a sequential Pd-catalyzed coupling-condensation-coupling (C3), a one-pot sequence which concatenates S
- Deni?en, Melanie,Nordmann, Jan,Dziambor, Julian,Mayer, Bernhard,Frank, Walter,Müller, Thomas J. J.
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p. 33838 - 33854
(2015/04/27)
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- Metal-free synthesis of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts
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A straightforward method for the preparation of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts has been developed. The one-pot reaction proceeds rapidly in the presence of a Lewis acid without exclusion of air and moisture.
- Taylor, Cassandra,Bolshan, Yuri
-
supporting information
p. 488 - 491
(2014/04/03)
-
- A Highly Active CuI/TMEDA Catalytic System for the Coupling Reaction of Acid Chlorides with Terminal Alkynes under Solvent-Free Conditions
-
A highly efficient copper(I) iodide/N,N,N′,N′-tetramethylethylenediamine (CuI/TMEDA) catalytic system for the synthesis of ynones has been developed. A variety of terminal alkynes, including 4-iodophenylacetylene, were smoothly coupled with acid chlorides
- Yin, Weiyan,He, Haifeng,Zhang, Yani,Luo, Di,He, Hongwu
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p. 2617 - 2621
(2015/12/26)
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- Gold-catalyzed 1,3-transposition of ynones
-
An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regio
- Kazem Shiroodi, Roohollah,Soltani, Mohammad,Gevorgyan, Vladimir
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supporting information
p. 9882 - 9885
(2014/08/05)
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- Anilines as substrates in consecutive four-component synthesis of novel 1-aryl-5-benzoyl-6-phenyl-3,4-dihydropyridin-2(1 H)-ones
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The consecutive four-component synthesis of 5-acylpyridin-2(1H)-ones initiated by a copper-free alkynylation in a one-pot fashion has been expanded to include considerably less nucleophilic anilines as the amine component in the Michael addition step by altering the solvent system to 1,4-dioxane; 17 examples for the synthesis of 1-aryl-5-benzoyl-6-phenyl-3,4-dihydropyridin-2(1H) -ones were obtained in moderate to good yields.
- Nordmann, Jan,Müller, Thomas J. J.
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supporting information
p. 522 - 530
(2014/03/21)
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- A facile and rapid route for the synthesis of Cu/Cu2O nanoparticles and their application in the Sonogashira coupling reaction of acyl chlorides with terminal alkynes
-
We have demonstrated a facile one-step synthetic strategy for the preparation of Cu/Cu2O nanoparticles (NPs) via a microwave method. The microwave energy acts as a driving force for the synthesis of Cu/Cu2O NPs, which makes the proce
- Bhosale, Manohar A.,Sasaki, Takehiko,Bhanage, Bhalchandra M.
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p. 4274 - 4280
(2015/01/09)
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- Palladium-, ligand-, and solvent-free synthesis of ynones by the coupling of acyl chlorides and terminal alkynes in the presence of a reusable copper nanoparticle catalyst
-
Supported copper nanoparticles are utilized for the first time as a highly efficient and reusable catalyst in the coupling of acyl chlorides and terminal alkynes to prepare various ynones. The reaction is carried out under palladium-, ligand-, and solvent
- Sun, Weijiang,Wang, Yan,Wu, Xuan,Yao, Xiaoquan
-
supporting information
p. 2356 - 2360
(2013/09/12)
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- Efficient consecutive four-component synthesis of 5-acylpyrid-2-ones initiated by copper-free alkynylation
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A one-pot, consecutive, four-component synthesis of 5-acylpyrid-2-ones initiated by Pd/cataCXium ABn catalysis proceeds under mild reaction conditions and in good yields, with a broad scope of three points of diversity. This sequence is superio
- Nordmann, Jan,Breuer, Natascha,Mueller, Thomas J. J.
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supporting information
p. 4303 - 4310
(2013/07/26)
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- A one-pot coupling-addition-cyclocondensation sequence (CACS) to 2-substituted 3-acylpyrroles initiated by a copper-free alkynylation
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A novel three-component synthesis of 2-substituted 3-acylpyrroles can be initiated by a copper-free Pd-catalyzed alkynylation in a one-pot fashion. The reaction sequence proceeds under mild reaction conditions and in moderate to good yields with a broad s
- Nordmann, Jan,Mueller, Thomas J. J.
-
supporting information
p. 6556 - 6561
(2013/09/24)
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- Synthesis of N-alkyl-substituted 4-quinolones via tandem alkenyl and aryl C-N bond formation
-
N-Alkyl-substituted 4-quinolones are present as the key structural motif in many marketed drugs. An efficient one-step tandem amination approach was developed to afford N-alkyl-substituted 4-quinolones in high yields from easily accessible o-chloroaryl acetylenic ketones and functionalized alkyl amines. The approach complements and extends our previous work. Compared with other reported methods, the current method provides a very simple and convenient route. Georg Thieme Verlag Stuttgart · New York.
- Shao, Jun,Huang, Xiaomei,Hong, Xiaohu,Liu, Bingxin,Xu, Bin
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p. 1798 - 1808
(2012/08/08)
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- Polystyrene-supported zinc bromide-ethylenediamine complex as a reusable and highly efficient heterogeneous catalyst for the synthesis of α,β-acetylenic ketones
-
A polystyrene-supported zinc bromide-ethylenediamine complex was shown to be useful as a recyclable heterogeneous catalyst for the rapid and efficient synthesis of ,-acetylenic ketones in good-to-excellent yields by cross-coupling of acid chlorides with t
- Keivanloo, Ali,Bakherad, Mohammad,Bahramian, Bahram,Rahmani, Mahrokh,Taheri, Sayed Ali Naghi
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experimental part
p. 325 - 329
(2011/03/18)
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- Palladium- and base-free synthesis of conjugated ynones by cross-coupling reactions of alkynylboronates with acid chlorides mediated by CuCl
-
Alkynylboronates can be employed as a practical and versatile precursor for a variety of π-conjugated organic compounds. In the presence of Cu(I) salt, cross-coupling reactions of acid chlorides with alkynylboronates giving rise to the corresponding conju
- Nishihara, Yasushi,Saito, Daisuke,Inoue, Eiji,Okada, Yoshiaki,Miyazaki, Mikihiro,Inoue, Yoshiaki,Takagi, Kentaro
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experimental part
p. 306 - 308
(2010/03/24)
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- Palladium-catalyzed tandem amination reaction for the synthesis of 4-quinolones
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(Figure presented) An efficient palladium-catalyzed tandem amlnatlon approach was developed In one step to afford functlonallzed 4-qulnolones In good to excellent ylelds from easlly accessible o-haloaryl acetylenlc ketones and primary amines.
- Zhao, Tlankun,Xu, Bin
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supporting information; experimental part
p. 212 - 215
(2010/03/24)
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- A copper- and solvent-free coupling of acid chlorides with terminal alkynes catalyzed by a polystyrene-supported palladium(0) complex under aerobic conditions
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A polystyrene-supported palladium(0) complex [PS-dpp-Pd(0)] is an efficient catalyst for the copper- and solvent-free acylation of terminal alkynes with different acid chlorides in the presence of triethylamine as base, giving the corresponding ynones in
- Bakherad, Mohammad,Keivanloo, Ali,Bahramian, Bahram,Rajaie, Mahbobeh
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experimental part
p. 33 - 35
(2010/03/04)
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- Heterocyclic analogs of thioflavones: Synthesis and NMR spectroscopic investigations
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The synthesis of several hitherto unknown heterocyclic ring systems derived from thioflavone is described. Coupling of various o haloheteroarenecarbonyl chlorides with phenylacetylene gives 1-(o-haloheteroaryl)-3-phenylprop-2-yn-1- ones, which were treate
- Fuchs, Ferdinand C.,Eller, Gernot A.,Holzer, Wolfgang
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experimental part
p. 3814 - 3832
(2010/03/03)
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- A novel consecutive three-component coupling-addition-SNAr (CASNAR) synthesis of 4H-thiochromen-4-ones
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4H-Thiochromen-4-ones and 4H-thiopyrano[2,3-b]pyridin-4-ones are readily synthesized in good yields by a consecutive one-pot, three-component coupling-addition-SNAr (CASNAR) sequence starting from aroyl chlorides, alkynes, and sodium sulfide no
- Willy, Benjamin,Müller, Thomas J. J.
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experimental part
p. 1255 - 1260
(2009/08/14)
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- 1,2-Disubstituted 4-quinolones via copper-catalyzed cyclization of 1-(2-halophenyl)-2-en-3-amin-1-ones
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1,2-Disubstituted 4-quinolones have been prepared via copper-catalyzed heterocyclization of 1-(2-bromophenyl)- and 1-(2-chlorophenyl)-2-en-3-amin-1- ones, readily obtained from α,β-ynones and primary amines. The reaction tolerates a variety of useful functionalities including ester, keto, cyano, and chloro substituents. Quinolone derivatives can also be prepared via a sequential process from α,β-ynones and primary amines, omitting the isolation of the 1-(2-halophenyl)-2-en-3-amin-1-one intermediates. Georg Thieme Verlag Stuttgart.
- Bernini, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Sferrazza, Alessio
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experimental part
p. 1209 - 1219
(2009/12/07)
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- L-Proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines
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Highly functionalized multisubstituted 1,4-dihydropyridines 5 have been concisely synthesized in moderate to good yields vial-proline-catalyzed one-pot multicomponent reactions (MCRs) of alkynoates or alkynones 1, amines 2, β-dicarbonyl compounds 3 and aldehydes 4 under mild conditions. The MCR process involves hydroamination/Knoevenagel condensation/Michael-type addition/intramolecular cyclization processes and leads to the formation of 1,4-dihydropyridines 5. The molecular structure of 5ckaa was confirmed by single-crystal X-ray diffraction. This method is energy saving and environmentally friendly, providing easy access to diverse multisubstituted polyfunctional 1,4-dihydropyridines. The Royal Society of Chemistry 2009.
- Jiang, Huanfeng,Mai, Ronghuan,Cao, Hua,Zhu, Qiuhua,Liu, Xiaohang
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experimental part
p. 4943 - 4953
(2010/02/16)
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