- Copper(i)-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphites
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Intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphite diesters proceeded in the presence of Cu(i)-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds are activated at once and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.
- Li, Guangzhe,Yu, Guo,Wang, Chengdong,Morita, Taiki,Zhang, Xuhai,Nakamura, Hiroyuki
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p. 113 - 116
(2021/12/29)
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- Polymerase-mediated synthesis ofp-vinylaniline-coupled fluorescent DNA for the sensing of nucleolin protein-c-mycG-quadruplex interactions
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In this paper we report the synthesis of two deoxyuridine derivatives (dUCN2,dUPy)—featuringp-vinylaniline-based fluorophores linked through a propargyl unit at the 5′ position—that function as molecular rotors. This probing system proved to be useful for the sensing of gene regulation arising from interactions between this G-quadruplex and nucleolin.
- Ravi Kumara, Guralamatta Siddappa,Seo, Young Jun
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p. 5788 - 5793
(2021/07/12)
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- Pyridoxine-resveratrol hybrids as novel inhibitors of MAO-B with antioxidant and neuroprotective activities for the treatment of Parkinson's disease
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A series of pyridoxine-resveratrol hybrids were designed and synthesized as monoamine oxidase B inhibitors for the treatment of Parkinson's disease. Most of them exhibited potent inhibitory activities on MAO-B with high selectivity. Specifically, compounds 12a, 12g and 12l showed the most excellent inhibition to hMAO-B with the IC50 values of 0.01 μM, 0.01 μM and 0.02 μM, respectively. Further reversibility study demonstrated that 12a and 12l were reversible and 12g was irreversible MAO-B inhibitors. Molecular docking studies of MAO revealed the binding mode and high selectivity of these compounds with MAO-B. In addition, these three representative compounds also exhibited low cytotoxicity and excellent neuroprotective effect in the test on H2O2-induced PC-12 cell injury. Moreover, 12a, 12g and 12l showed good antioxidant activities and high blood-brain barrier permeability. Overall, all of these results highlighted 12a, 12g and 12l were potential and excellent MAO-B inhibitors for PD treatment.
- Cao, Zhongcheng,Deng, Yong,Li, Wei,Shi, Yichun,Song, Qing,Yang, Xia,Zhang, Li
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- Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N -propargylanilines with diverse carbon pronucleophiles: Facile access to functionalized tetrahydroquinolines
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Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with two types of carbon pronucleophiles (nitromethane as a sp3 carbon pronucleophile and phenylacetylenes as sp carbon pronucleophiles) proceeded to give the 2-substituted tetrahydroquinolines in good yields with 100percent atomic utilization without any additional external oxidants.
- Li, Guangzhe,Wang, Chengdong,Li, Yueqing,Shao, Kun,Yu, Guo,Wang, Shisheng,Guo, Xiuhan,Zhao, Weijie,Nakamura, Hiroyuki
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p. 7333 - 7336
(2020/07/23)
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- Ethyl lactate as a renewable carbonyl source for the synthesis of diynones
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Ethyl lactate, a sustainable feedstock, serves as a highly attractive building block for the synthesis of value-added chemicals such as skipped diynones and, after gold-catalyzed transposition, conjugated diynones. Green solvents are involved in all steps
- Solas, Marta,Suárez-Pantiga, Samuel,Sanz, Roberto
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supporting information
p. 213 - 218
(2019/01/28)
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- One-pot facile synthesis, crystal structure and antifungal activity of 1,2,3-triazoles bridged with amine-amide functionalities
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A library of twenty five 1,2,3-triazoles bridged with amine-amide functionalities have been synthesized from reaction of N-substituted(prop-2-yn-1-yl)amines (2a–2e), 2-bromo-N-arylacetamides (4a–4e) and sodium azide through copper(I)-catalyzed alkyne-azide cycloaddition. The synthesized compounds were characterized by using FTIR, 1H NMR, 13C NMR, and HRMS techniques. The structures of synthesized 5a (CCDC 1569245) and 5h (CCDC 1569249) were also confirmed by X-ray crystallography. Antifungal evaluation of newly synthesized triazoles was carried out against–Candida albicans and Aspergillus niger. Biological screening of synthesized 1,2,3-triazoles revealed moderate to good antifungal activity against tested strains.
- Kaushik,Luxmi, Raj,Kumar, Mukesh,Singh, Dharmendra,Kumar, Krishan,Pahwa, Ashima
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supporting information
p. 118 - 128
(2019/01/24)
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- One-pot synthesis of substituted-amino triazole-glycosides
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This work combined three classes of compounds in the same molecule “amino triazole-glycoside” and developed a convenient method for the synthesis of this type of compound via a one-pot two step reaction. Alkylation of amine derivatives with propargyl bromide to give propargylamine was performed in the first step subsequently followed by a ‘click’ reaction with various β-azido-glycosides in the presence of CuI in aqueous solution to provide β-amino triazole-glycosides. Thirty-two examples of glycosides were obtained in moderate to good yield using this one-pot procedure.
- Sutcharitruk, Warapond,Sirion, Uthaiwan,Saeeng, Rungnapha
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- Copper catalysed alkynylation of tertiary amines with CaC2: Via sp3 C-H activation
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A mild and easy-to-handle protocol to produce propargylamines with a terminal alkyne through catalytic cross-coupling of tertiary amines and calcium carbide has been developed. The reaction proceeds via sp3 C-H bond activation and C-C coupling. Good to excellent yields were obtained for the corresponding propargylamines with both alkyl and aryl substitutions. The development of these functionalized propargylamines with a terminal alkyne group will offer a wider application for the synthesis of natural or pharmaceutical products due to their unique sp C-H reactivity.
- Teong, Siew Ping,Yu, Dingyi,Sum, Yin Ngai,Zhang, Yugen
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supporting information
p. 3499 - 3502
(2016/07/06)
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- Synthesis of 2-Indolyltetrahydroquinolines by Zinc(II)-Catalyzed Intramolecular Hydroarylation-Redox Cross-Dehydrogenative Coupling of N-Propargylanilines with Indoles
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An intramolecular hydroarylation-redox cross-dehydrogenative coupling (CDC) of propargylic anilines with indoles proceeded in the presence of zinc(II) catalysts to give 2-indolyltetrahydroquinolines in good to high yields. Three C-H bonds (two sp2and one sp3) are activated in one shot and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.
- Li, Guangzhe,Nakamura, Hiroyuki
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p. 6758 - 6761
(2016/06/09)
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- Convergent synthesis and properties of photoactivable NADPH mimics targeting nitric oxide synthases
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A new series of photoactivable NADPH mimics bearing one or two O-carboxymethyl groups on the adenosine moiety have been readily synthesized using click chemistry. These compounds display interesting one- or two-photon absorption properties. Their fluorescence emission wavelength and quantum yields (Φ) are dependent on the solvent polarity, with a red-shift in a more polar environment (λmax,em = 460-467 nm, Φ > 0.53 in DMSO, and λmax,em = 475-491 nm, Φ 0.17 in Tris). These compounds show good binding affinity towards the constitutive nNOS and eNOS, confirming for the first time that the carboxymethyl group can be used as a surrogate of phosphate. Two-photon fluorescence imaging of nanotriggers in living cells showed that the presence of one carboxymethyl group (especially on the 3′ position of the ribose) strongly favors the addressing of nanotriggers to eNOS in the cell context.
- Nguyen,Bogliotti,Chennoufi,Henry,Tauc,Salas,Roman,Slama-Schwok,Deprez,Xie
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p. 9519 - 9532
(2016/10/22)
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- Synthesis of polyfunctional triethoxysilanes by 'click silylation'
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The copper-catalyzed 'click silylation' has been exploited for the chemical modification of γ-azidopropyltriethoxysilane (AzPTES) with a wide range of terminal alkynes (1a-1v) in a one-pot operation. The novel 1,2,3-triazole-triethoxysilane derivatives (2a-2v) were synthesized by this procedure and comprehensively characterized by IR spectra, 1H and 13C NMR, and HRMS studies.
- Singh, Gurjaspreet,Mangat, Satinderpal Singh,Singh, Jandeep,Arora, Aanchal,Sharma, Ramesh K.
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supporting information
p. 903 - 909
(2015/03/03)
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- Metal-free catalyst for the chemoselective methylation of amines using carbon dioxide as a carbon source
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N-methylation of amines is an important step in the synthesis of many pharmaceuticals and has been widely applied in the preparation of other key intermediates and chemicals. Therefore, the development of efficient methylation methods has attracted considerable attention. In this respect, carbon dioxide is an attractive C1 building block because it is an abundant, renewable, and nontoxic carbon source. Consequently, we developed a highly chemoselective, metal-free catalytic system that operates under ambient conditions for the N-methylation of amines. The methylation of amines with CO2 as C1 source and Ph2SiH2 as reducing agent was achieved with an N-heterocyclic carbene (NHC) as the catalyst. The catalyst is tolerant toward a variety of functional groups (including esters and ethers, nitro, nitrile, and carbonyl groups, and unsaturated C-C bonds); the reaction uses commercially available reagents and can be performed on a gram scale.
- Das, Shoubhik,Bobbink, Felix D.,Laurenczy, Gabor,Dyson, Paul J.
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supporting information
p. 12876 - 12879
(2016/02/18)
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- Synthesis of substituted 3-indolylimines and indole-3-carboxaldehydes by rhodium(II)-catalyzed annulation
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An efficient Cu/Rh-catalyzed method is proposed for the synthesis of 3-indolylimines from N-propargylanilines through Rh(II)-catalyzed denitrogenative annulation of N-sulfonyl-1,2,3-triazoles. Further combined with hydrolysis or reduction, a one-pot method is developed to enable the direct incorporation of an imine, aldehyde, or amine group into an indole system from an alkyne. A variety of substituted 3-indolylimines, indole-3-carboxaldehydes, and 3-Indolylmethanamines are synthesized in good yields.
- Rajagopal, Basker,Chou, Chih-Hung,Chung, Ching-Cheng,Lin, Po-Chiao
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p. 3752 - 3755
(2014/08/05)
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- Facile One-Pot Synthesis of 1,2,3-Triazoles Featuring Oxygen, Nitrogen, and Sulfur Functionalized Pendant Arms
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A practical and efficient one-pot synthesis of novel 1,2,3-triazoles featuring nitrogen, oxygen, and sulfur functionalized pendant arms has been developed. The click reaction of mono-propargyl derivatives supported by aniline, thiophenol, and benzyl alcohol, with sodium azide and p-substituted benzyl halogenides, renders a series of N-substituted-1,2,3-triazoles in good yields under mild reaction conditions. The catalyst system was based in Cu(OAc)2·H2O, sodium L-ascorbate, and 1,10-phenanthroline monohydrate, and all reactions were performed in a mixture H2O-ethanol (4:1 v/v). Additionally, the preparation of bis-1,2,3-triazoles supported by di-propargylated aniline was carried out, demonstrating the versatility of the present methodology. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Mendoza-Espinosa, Daniel,Negron-Silva, Guillermo,Lomas-Romero, Leticia,Gutierrez-Carrillo, Atilano,Santillan, Rosa
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p. 807 - 817
(2014/03/21)
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- Copper(II)-catalyzed silylation of activated alkynes in water: Diastereodivergent access to E- or Z-β-silyl-α,β-unsaturated carbonyl and carboxyl compounds
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Copper(II)-catalyzed silylation of substituted alkynylcarbonyl compounds was investigated. Through the activation of Me2PhSiBpin in water at room temperature and open atmosphere, vinylsilanes conjugated to carbonyl groups are synthesized in high yield. A surprising diastereodivergent access to olefin geometry was discovered using a silyl conjugate addition strategy: aldehydes and ketones were Z selective while esters and amides were exclusively transformed into the E products. Dial a diastereomer: The title reaction proceeds through the activation of Me2PhSiBpin in water at room temperature and open atmosphere to produce high yields of vinylsilanes conjugated to carbonyl groups. A surprising diastereodivergent access to olefin geometry was discovered using this silyl conjugate addition strategy: aldehydes were Z selective while esters and amides exclusively delivered the E-configured products.
- Calderone, Joseph A.,Santos, Webster L.
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supporting information
p. 4154 - 4158
(2014/05/06)
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- Synthesis of polyfunctional triethoxysilanes by 'click silylation'
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The copper-catalyzed 'click silylation' has been exploited for the chemical modification of γ-azidopropyltriethoxysilane (AzPTES) with a wide range of terminal alkynes (1a-1v) in a one-pot operation. The novel 1,2,3-triazole-triethoxysilane derivatives (2a-2v) were synthesized by this procedure and comprehensively characterized by IR spectra, 1H and 13C NMR, and HRMS studies.
- Singh, Gurjaspreet,Mangat, Satinderpal Singh,Singh, Jandeep,Arora, Aanchal,Sharma, Ramesh K.
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supporting information
p. 903 - 909
(2014/02/14)
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- Intramolecular annulation of aromatic rings with N-sulfonyl 1,2,3-triazoles: Divergent synthesis of 3-methylene-2,3-dihydrobenzofurans and 3-methylene-2,3-dihydroindoles
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The controllable synthesis of 3-methylene-2,3-dihydrobenzofurans 2 and 3-methylene-2,3-dihydroindoles 5 has been developed through Rh-catalyzed intramolecular annulation of aromatic rings with azavinyl carbenes. This journal is
- Tang, Xiang-Ying,Zhang, Yong-Sheng,He, Lv,Wei, Yin,Shi, Min
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supporting information
p. 133 - 136
(2015/01/09)
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- Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation: C-H versus C-C cleavage in TMEDA
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Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation reactions have been achieved under facile and mild conditions. TMEDA coupled with various terminal alkynes via C-H bond cleavage in good yields using atmospheric oxygen as an oxidant. Switching from air to TBHP afforded aminomethylation products of terminal alkynes through C-C bond cleavage of TMEDA. The protocol provided a novel strategy to prepare bi/tridentate N-ligand.
- Shen, Qi,Zhang, Lei,Zhou, Yu-Ren,Li, Jian-Xin
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supporting information
p. 6725 - 6728
(2013/11/19)
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- A facile method for the stereoselective preparation of (1E,3E)-4-substituted-1-amino-1,3-dienes via 1,4-elimination
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The 1,4-elimination reaction of 1-amino-4-methoxy-(2Z)-alkenes is shown to proceed with high (1E,3E)-stereoselectivities to afford the corresponding 4-substituted-1-amino-1,3-dienes in good yield. The scope and stereochemical features of the synthetic met
- Tayama, Eiji,Sugai, Sayaka
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p. 6163 - 6166
(2008/03/12)
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- Prototropic rearrangement of 2-propynyl(methyl)amino, 2-propynyloxy, and 2-propynylsulfanyl derivatives of hetarenes under conditions of phase-transfer catalysis: Mechanism and limitations
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2-Propynyl derivatives of N-methylaniline, phenol, benzenethiol, 2-pyridinethiol, 2-pyrimidinethiol, and 1,3-benzoxazole-2-thiol were synthesized. Under conditions of phase-transfer catalysis, phenyl 2-propynyl sulfide is converted into allenyl phenyl sul
- Rubina,Fleisher,Abele,Popelis,Lukevits
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p. 963 - 967
(2007/10/03)
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- 4-Aminobut-2-yne carboxylic acid derivatives and their use as antimicrobial agents
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There are described 4-aminobut-2-ynecarboxylic acid derivatives of formula whereinR1 and R2are each independently of the other hydrogen, C1-C20alkyl; C3-C12cycloalkyl; unsubstituted or Csu
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- A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates
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1-(α-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylaluminates to give propargylic amines in excellent yields, including unsubstituted N,N-dialkyl propargylamines, which are difficult to obtain from lithium acetylide. The reaction of α-benzotriazolyl alkyl ethers and sodium dialkynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared via the desilylation of trimethylsilylpropargyl ethers.
- Ahn, Jin Hee,Joung, Meyoung J.,Yoon, Nung Min,Oniciu, Daniela C.,Katritzky, Alan R.
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p. 488 - 492
(2007/10/03)
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- BEHAVIOR OF PROPARGYL- AND ALLYLPROPARGYL-AMMONIUM SALTS IN AQUEOUS ALKALINE MEDIUM. SYNTHESIS OF 2-METHYL-2-PHENYLBENZISOINDOLINIUM AND 2-METHYL-2-PHENYLISOINDOLINIUM SALTS
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Methylphenylpropargyl-(3-phenylpropargyl)-ammonium bromide salts are cyclized almost quantitatively under base-catalysis conditions with the formation of 2-methyl-2-phenylbenzisoindolinium bromide.The allyl analog is subject to rearrangement-decomposit
- Chukhadzhyan, E. O.,Manasyan, L. A.,Chukhadzhyan, El. O.,Shakhatuni, K. G.,Babayan, A. T.
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- Intramolecular aromatic substitution and amino-claisen rearrangement in substituted N-(2-propynyl)anilines on electron impact
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N-(2-Propynyl)anilines undergo amino-Claisen rearrangement to a minor extent in the ion source, losing a molecule of HCN under electron impact conditions. However, metastable molecular ions with energies closer to threshold undergo Claisen rearrangement g
- Ramana,Sudha
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p. 1028 - 1033
(2007/10/03)
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- HYDROBORATION D'AMINES INSATUREES-IV; HYDROBORATION-ALKYLATION DE PROPARGYLAMINES PAR DES DIALKYLBORANES MIXTES
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Hydroboration-alkylation of substituted or unsubstituted propargylamines with thexylalkylboranes rapidly gives good yields of ethylenic amines.A tendency towards rearranged products depends on the basicity of the starting acetylenic amines.Comparatively t
- Torregrosa, J. L.,Baboulene, M.,Speziale, V.,Lattes, A.
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p. 3101 - 3106
(2007/10/02)
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- The Pyrolysis of N-Allyl Compounds: Free-radical and Retro-ene Mechanisms
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Flash vacuum pyrolysis of N-alkyl-N-allylanilines gives imines by free radical cleavage of the allyl group followed by loss of an atom (or group of atoms) from the α-carbon atom of the alkyl group.The corresponding N-propargyl derivatives also give imines on pyrolysis, but the mechanism is a concerted retro-ene process which may lead to different products from the corresponding N-allyl compound.N-Allyl-N,N-dialkylamines also decompose thermally by a retro-ene process
- Cadogan, J. I. G.,Hickson, Clare L.,McNab, Hamish
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p. 2247 - 2273
(2007/10/02)
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- HYDROBORATION D'AMINES INSATUREES-II REGIO ET STEREOSELECTIVITE DE L'HYDROBORATION-ALKYLATION D'AMINES ACETYLENIQUES
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The hydroboration reaction of acetylenic amines R1R2N-CH(R3)-CC-R4 was studied.We report the first results of a study of the reactivity of dialkylborane R2BH towards these amines which allow us to propose a new method for the synthesis of differently substituted β-ethylenic amines.The regioselectivity and the stereoselectivity of this reaction are examined and allow us to set out the possibility of a trans hydroboration.
- Torregrosa, J. L.,Baboulene, M.,Speziale, V.,Lattes, A.
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p. 2355 - 2363
(2007/10/02)
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