4354-73-8Relevant articles and documents
Studies on the reaction of cycloalkanones with malonodinitrile
Abdelrazek, Fathy M.,Metwally, Nadia H.,Kassab, Nazmi A.,Jaafar, Mohammed T.,Metz, Peter,J?ger, Anne
, p. 1785 - 1790 (2014)
Cyclopentanone reacts with malononitrile catalyzed by piperidine or sodium acetate to afford under any case cyclopentylidenemalononitrile dimer: 5-aminospiro-[2,6,7,7a-tetrahydroindene-7,1′-cyclopentane]-4,6,6-tricarbonitrile (7) as the sole product. Contrary to this behavior, cyclohexanone reacts with malononitrile catalyzed by piperidine to afford the analogous cyclohexylidenemalononitrile dimer: 2-aminospiro-[3,4,5,6,7,4a-hexahydronaphthalene-4,1′-cyclohexane]-1,3,3-tricarbonitrile (11); whereas when the reaction is catalyzed by sodium acetate, it afforded 9,10-diaza-8,11-dioxo-tricyclo-[4.3.3.01,6]-dodecane-7,12-dicarbonitrile (12). The structures of these products were established on the basis of their elemental analysis and spectral data, and plausible mechanism has been postulated to account for their formation. X-ray crystallography was carried out as a further evidence for structures 7 and 12.
Homogeneous-like solid base catalysts based on pyridine-functionalized swelling porous polymers
Zhang, Yong-Lai,Liu, Sen,Liu, Siyu,Liu, Fujian,Zhang, Haiyan,He, Yinyan,Xiao, Feng-Shou
, p. 1212 - 1217 (2011)
Reported here is the synthesis of pyridine-functionalized porous polymers, which are designed as homogeneous-like base catalysts. These highly porous catalysts have adjustable pyridine contents, high BET surface area (312-649 m2/g), large pore
Catalytic performance of a new 1D Cu(II) coordination polymer {Cu(NO3)(H2O)}(HTae)(4,4'-Bpy) for Knoevenagel condensation
Larrea, Edurne S.,De Luis, Roberto Fernández,Arriortua, María I.
, (2016)
The {Cu(NO3)(H2O)}(HTae)(4,4'-Bpy) (H2Tae = 1,1,2,2-tetraacetylethane, 4,4'-Bpy = 4,4'-Dipyridyl) 1D coordination polymer has been obtained by slow evaporation. The crystal structure consists of parallel and oblique {Cu(HT
Ultra-high concentrations of amino group functionalized nanoporous polymeric solid bases: Preparation, characterization and catalytic applications
Zhang, Bin,Liu, Chen,Wang, Lingjing,Yi, Xianfeng,Zheng, Anmin,Deng, Wenshu,Qi, Chenze,Liu, Fujian
, p. 25 - 30 (2015)
We report here that the amino-group functionalized nanoporous polydivinylbenzene (PDVB-2.0-NH2, PDVB-NH2), acts as an efficient solid base for catalyzing Knoevenagel condensation, which could be synthesized from nitration of nanoporo
Organic reactions in ionic liquids: Gewald synthesis of 2-aminothiophenes catalyzed by ethylenediammonium diacetate
Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
, p. 3801 - 3806 (2004)
Ionic liquids based on 1-butyl-3-methylimidazolium tetrafluoroborate (BmimBF4) and 1-butyl-3-methylimidazolium hexafluorophosphate (BmimPF6) were used as reusable alternatives to volatile organic solvents (VOCs) for ethylenediammonium diacetate (EDDA) catalyzed Gewald synthesis of 2-aminothiophenes. Significant rate enhancement and improvement of the yield were observed. The ionic liquids containing catalyst EDDA were recycled several times with no decreases in yields and reaction rates.
Interplay between hydrophobicity and basicity toward the catalytic activity of isoreticular MOF organocatalysts
Abedi, Sedigheh,Azhdari Tehrani, Alireza,Ghasempour, Hosein,Morsali, Ali
, p. 6970 - 6976 (2016)
Due to the structural diversity of metal-organic frameworks, MOFs, tailored engineering of these compounds is important for their use in catalytic processes. Among the MOFs tested as heterogeneous catalysts, there have been rare reports of size selective catalysts. In the present work, we could successfully indicate that subtle substrate selectivity can be induced in the catalytic system by designing a series of isoreticular MOFs with slight structural modifications. Four MOF catalysts possessing imine and/or amine basic N-donor pillars bearing phenyl or naphtyl cores showing different hydrophobic characters around the basic reaction center were prepared via a simple mechano-chemical synthesis. They were characterized thoroughly using TG, IR and PXRD analysis. For the first time, the aldol-type condensation reaction of malononitrile with ketone-functionalized carbonyl substrates was developed in the presence of the basic MOF organocatalysts. Moreover, it has been successfully shown that a subtle substrate selectivity can be addressed during the reaction of three slightly different α,β-unsaturated carbonyl compounds in contrast to the effect of size control barriers that commonly direct a heterogeneous reaction pathway.
Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds
Wu, Hui-Chun,Wang, Chen,Chen, Ying-Han,Liu, Yan-Kai
supporting information, p. 1762 - 1765 (2021/02/27)
An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary stereocenter with excellent stereoselectivities.
Synthesis of 1H-isochromenes, 4H-chromenes, and ortho-aminocarbonitrile tetrahydronaphthalenes from the same reactants by using metal-free catalyst
Naeimi, Hossein,Mohammadi, Somaye
supporting information, p. 50 - 59 (2019/12/27)
A facile and rapid multicomponent synthesis of pharmaceutically diverse 1H-isochromenes, 4H-chromenes, and ortho-aminocarbonitrile tetrahydronaphthalenes has been developed from benzaldehyde, malononitrile, and cyclohexanone. Three different methods from the same reactants, solvent, temperature, and catalyst lead to three products with excellent yields. All the reactions were followed with the Michael addition and cyclization. In this study, morpholine was used as an active metal-free base catalyst that increases the yields of products and decreases the time of reactions.
