- Oxidative Olefination of Benzylamine with an Active Methylene Compound Mediated by Hypervalent Iodine (III)
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Hypervalent iodine-mediated oxidative olefination of amines with an active methylene compound provides a rapid gateway towards the formation of electrophilic alkenes under mild reaction conditions in good to excellent yields. This is an efficient protocol for the preparation of substituted electrophilic alkenes.
- Rupanawar, Bapurao D.,Veetil, Sruthi M.,Suryavanshi, Gurunath
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- Green synthesis of a nano salt and its application as multifunctional organocatalyst for Knoevenagel condensation
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1,2-Ethanediammonium 3-hydroxypropane-1-sulfonate [(EDA)(HPS)] as a novel nano multifunctional organosalt was synthesized via a simple and green chemical route and characterized using various techniques such as proton nuclear magnetic resonance (1/s
- Honarmand, Moones
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- Zirconium-mediated multicomponent reactions of 1,3-butadiynes with ylidenemalononitriles to form functionalized 1,8-naphthyridine and cyclopenta[b]pyridine derivatives
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Zirconocene-mediated multicomponent reactions of 1,3-butadiynes with ylidenemalononitriles in the absence or presence of CuCl have been developed. In the absence of CuCl, 1,3-butadiyne couples with three molecules of ylidenemalononitriles to yield azazirconacycles bearing a hexahydro-1,8-naphthyridine skeleton with high stereoselectivity. In the presence of CuCl, cyclopenta[b]-pyridine or cyclopenta[ b ]quinolin-1-one derivatives are obtained via transmetalation of Zr-C bond to Cu-C bond as the key reaction step. These domino-type reactions proceed with high chemo-, regio- and/or stereoselectivities, and allowing the formation of multiple C-N and C-C bonds in a single operation.
- Yu, Shasha,Sun, Renhong,Chen, Haoyi,Xie, Xin,Liu, Yuanhong
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- Silica gel catalysed Knoevenagel condensation in dry media under microwave irradiation
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Neutral silica gel catalysed efficiently the Knoevenagel condensation of carbonyl compounds on malononitrile in dry media under microwave irradiation. Synergy between dry media and microwaves is shown.
- De La Cruz, Pilar,Diez-Barra, Enrique,Loupy, Andre,Langa, Fernando
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- Montmorillonite K-10 catalyzed Knoevenagel condensation under microwave irradiation in solventless system
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Montmorillonite K-10 catalyzed efficiently the Knoevenagel condensation of carbonyl compounds with malonitrile and ethylcyanoacetate in dry media under microwave irradiation.
- Heravi, Majid M.,Tajbakhsh, Mahmood,Mohajerani, Bagher,Ghassemzadeh, Mitra
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- The Knoevenagel condensation using quinine as an organocatalyst under solvent-free conditions
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The Knoevenagel condensation between active methylene compounds and aromatic carobonyl compounds has been developed using quinine as an organocatalyst to afford various electrophilic alkenes in excellent yields (up to 90%). In the presence of a catalytic amount of quinine (15 mol%), the reaction proceeded at room temperature (RT) under solvent-free conditions. In this green approach, the organocatalyst was recovered and recycled for up to four cycles without appreciable loss of activity.
- Jain, Kavita,Chaudhuri, Saikat,Pal, Kuntal,Das, Kalpataru
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supporting information
p. 1299 - 1304
(2019/01/21)
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- Sterically congested ester formation from α-substituted malononitrile and alcohol by an oxidative method using molecular oxygen
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A metal-free oxidative esterification or thio-esterifica-tion of readily available substituted malononitrile and alcohol or thiol has been developed by simply mixing α-substituted malononitrile and alcohol or thiol in the presence of base under a molecular oxygen atmosphere. Sterically hindered ester or thioester can be prepared efficiently.
- Hayashi, Yujiro,Li, Jing,Asano, Hirotaka,Sakamoto, Daisuke
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supporting information
p. 675 - 677
(2018/11/23)
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- Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles
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A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions wit
- Liu, Yingtian,Dang, Xinxin,He, Yu,Bai, Hudong,Chen, Xuehong,Li, Jun-Long,Fan, Junting,Jiang, Hezhong,Li, Jiahong
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p. 662 - 671
(2019/02/20)
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- Knoevenagel Condensation of Aldehydes and Ketones with Malononitrile Catalyzed by Amine Compounds-Tethered Fe3O4@SiO2 Nanoparticles
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Abstract: A new magnetic nanoparticle supported-catalyst was developed for the Knoevenagel condensation between malononitrile and several aldehydes. The Fe3O4@SiO2-3N (where 3N = N1-(3-trimethoxysilylpropyl)diet
- de Resende Filho, Jo?o Batista M.,Pires, Gilvan P.,de Oliveira Ferreira, Jo?o Marcos Gomes,Teotonio, Ercules E. S.,Vale, Juliana A.
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p. 167 - 180
(2017/02/10)
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- Dual functionalization of porous aromatic frameworks as a new platform for heterogeneous cascade catalysis
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Dual functionalization of porous aromatic frameworks (PAFs) has been illustrated in the context of incorporating two antagonistic sites of strong acid and strong base into the highly porous and highly robust PAF-1 via stepwise post-synthetic modification. The resulting bifunctionalized PAF-1 exhibits excellent performances in catalyzing a series of cascade reactions and demonstrates superior chemical stability compared to the counterparts of mesoporous silica and MOFs, thereby opening the door for dual functionalization of PAFs as a new platform for heterogeneous cascade catalysis. the Partner Organisations 2014.
- Zhang, Yiming,Li, Baiyan,Ma, Shengqian
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supporting information
p. 8507 - 8510
(2014/07/22)
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- Determination of thermodynamic affinities of various polar olefins as hydride, hydrogen atom, and electron acceptors in acetonitrile
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A series of 69 polar olefins with various typical structures (X) were synthesized and the thermodynamic affinities (defined in terms of the molar enthalpy changes or the standard redox potentials in this work) of the polar olefins obtaining hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the polar olefins (X ?-) obtaining protons and hydrogen atoms, and the thermodynamic affinities of the hydrogen adducts of the polar olefins (XH?) obtaining electrons in acetonitrile were determined using titration calorimetry and electrochemical methods. The pure Ci - 'C π-bond heterolytic and homolytic dissociation energies of the polar olefins (X) in acetonitrile and the pure Ci - 'C π-bond homolytic dissociation energies of the radical anions of the polar olefins (X?-) in acetonitrile were estimated. The remote substituent effects on the six thermodynamic affinities of the polar olefins and their related reaction intermediates were examined using the Hammett linear free-energy relationships; the results show that the Hammett linear free-energy relationships all hold in the six chemical and electrochemical processes. The information disclosed in this work could not only supply a gap of the chemical thermodynamics of olefins as one class of very important organic unsaturated compounds but also strongly promote the fast development of the chemistry and applications of olefins.
- Cao, Ying,Zhang, Song-Chen,Zhang, Min,Shen, Guang-Bin,Zhu, Xiao-Qing
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p. 7154 - 7168
(2013/08/23)
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- Study on comparison of reducing ability of three organic hydride compounds
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Selective reduction of three kinds of substrates were studied to evaluate the reducing abilities of N,N-dimethyl-benzimidazolidine (DMBI), 2-phenylbenzimidazoline (PBI) and 2-phenylbenzothiazoline (PBT). As hydride donors, these three five-membered heterocyclic compounds performed different reducing abilities depending on the substrates.
- Feng, Yi-Si,Yang, Chun-Yan,Huang, Qiang,Xu, Hua-Jian
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body text
p. 5053 - 5059
(2012/07/28)
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- Facile metal free regioselective transfer hydrogenation of polarized olefins with ammonia borane
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Transfer hydrogenation of polarized olefins bearing strongly electron-withdrawing groups on one side of the double bond was achieved with ammonia borane under mild conditions without using a catalyst. Mechanistic studies proved the character of the direct H transfers proceeding stepwise with a unique hydroboration intermediate and hydride before proton transfer.
- Yang, Xianghua,Fox, Thomas,Berke, Heinz
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supporting information; experimental part
p. 2053 - 2055
(2011/03/22)
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- CO2 absorbing cost-effective ionic liquid for synthesis of commercially important alpha cyanoacrylic acids: A safe process for activation of cyanoacetic acid
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Cost-effective and carbon dioxide absorbing ionic liquid, tri-(2-hydroxyethyl) ammonium acetate, was shown to perform multiple roles in Knoevenagel condensation. It acted as an environmentally benign solvent, as an activating catalyst for the less reactive cyanoacetic acid and also as a risk reduction medium for the unevenly generated large amount of CO2 gas for large scale reactions. The reaction was scaled up for multi-gram synthesis of commercially important alpha cyanoacrylic acids.
- Sharma, Yogesh O.,Degani, Mariam S.
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experimental part
p. 526 - 530
(2010/04/23)
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- A practical Knoevenagel condensation catalysed by imidazole
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The Knoevenagel condensation of aldehydes with active methylene compounds is easily carried out in dichloromethane using imidazole as an inexpensive catalyst. The olefinic products were obtained in high to excellent yields.
- Heravi, Majid M.,Tehrani, Maryam H.,Bakhtiari, Khadijeh,Oskooie, Hossein A.
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p. 561 - 562
(2007/10/03)
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- Use of isopropyl alcohol as a solvent in Ti(O-i-Pr)4-catalyzed Kn?evenagel reactions
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Kn?evenagel reactions of aldehydes and ketones with malononitrile, isopropyl cyanoacetate and diisopropyl malonate catalyzed by Ti(O-i-Pr) 4 proceeded smoothly in i-PrOH to give the corresponding reaction products in good to high yield. 3-Substituted coumarins were prepared by the present method.
- Yamashita, Kohei,Tanaka, Takanori,Hayashi, Masahiko
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p. 7981 - 7985
(2007/10/03)
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- I-oxo-3-aryl-1H-indene-2-carboxylic acid derivatives as selective inhibitors of fibroblast growth factor receptor-1 tyrosine kinase
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Fibroblast growth factor receptor (FGFr) mediated signal transduction is implicated in vascular proliferative diseases and some cancers. We have identified methyl 1-oxo-3-phenyl-1H-indene-2-carboxylic ester as a small molecule inhibitor of the tyrosine ki
- Barvian,Panek,Lu,Kraker,Amar,Hartl,Hamby,Showalter
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p. 2903 - 2908
(2007/10/03)
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- SYNTHESIS AND CHEMICAL REACTIVITY OF 4,4-DISUBSTITUTED PYRANAMINES
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The synthesis of a variety of 4,4-disubstituted 4H-pyranamines from alkylarylpropenenitriles and benzoylacetonitrile is reported.The reaction requirements demanded a different approach from the general synthesis of 2-amino-4H-pyrans.Electronic and steric
- Martin-Leon, Nazario,Segura, Jose L.,Seoane, Carlos,Soto, Jose L.
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p. 2434 - 2452
(2007/10/02)
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- Photochemical Reactions of 1,1-Diphenylpolycyanocyclopropanes in the Presence of Amines. Formal Extrusion of Dicyanomethylene
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Irradiation of 1,1,2,2-tetracyano-3,3-diphenylcyclopropane in the presence of triethylamine results in the formation of 1,1-dicyano-2,2-diphenylethylene, which is suggested to be formed as a result of spontaneous 1,2 elimination of stabilized ion pairs in the initially formed amine-cyclopropane adducts.
- Tomioka, Hideo,Kanda, Masahiko
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p. 2223 - 2226
(2007/10/02)
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- Mass Spectra of Dicyanomethylene Derivatives of Benzophenone Analogs
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The dicyanomethylene derivative of a benzophenone analog significantly alters the fragmentation pattern observed during electron impact ionization of the underivatized parent compound.A double bond connecting the dicyanomethylene moiety to the parent comp
- Wang, Ching-Bore,Her, Guor-Rong,Watson, J. Throck
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p. 457 - 461
(2007/10/02)
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