144467-12-9Relevant academic research and scientific papers
Access to 2-Amino-3-Arylthiophenes by Base-Catalyzed Redox Condensation Reaction Between Arylacetonitriles, Chalcones, and Elemental Sulfur
Nguyen, Thi Thu Tram,Le, Van Anh,Retailleau, Pascal,Nguyen, Thanh Binh
supporting information, p. 160 - 165 (2019/12/11)
A straightforward access to 2-amino-3-arylthiophenes has been developed via one-pot two-step three-component reaction of arylacetonitriles, chalcones and elemental sulfur. The first step consists of a DBU-catalyzed formation of Michael adduct between aryl
Reconstructed hydrotalcite as a highly active heterogeneous base catalyst for carbon-carbon bond formations in the presence of water
Ebitani, Kohki,Motokura, Ken,Mori, Kohsuke,Mizugaki, Tomoo,Kaneda, Kiyotomi
, p. 5440 - 5447 (2007/10/03)
The aldol reaction of carbonyl compounds is efficiently catalyzed by reconstructed hydrotalcites, obtained by treating the Mg-Al mixed oxide with water, as solid base catalysts in the presence of water. The catalysis of the reconstructed hydrotalcites is attributable to the surface base sites, created during the organization of the layered structure, with uniformly distributed strength. Furthermore, the reconstructed hydrotalcites provide a unique acid-base bifunctional surface capable of promoting the Knoevenagel and Michael reactions of nitriles with carbonyl compounds.
Reaction of metalated nitriles with enones
Reich, Hans J.,Biddle, Margaret M.,Edmonston, Robert J.
, p. 3375 - 3382 (2007/10/03)
(Chemical Equation Presented) There have been a number of reports of the kinetic conjugate (1,4) addition of metalated arylacetonitriles to enones. Several proposals have been made to explain this behavior based on nucleophile structure or aggregation state or on the HSAB properties of the reactants. A reexamination of these studies showed that in each case the 1,4 adducts resulted from equilibration of the kinetically formed 1,2 adducts to the more stable 1,4 adducts. Thus, no conclusions about the origins of 1,4 selectivity can be drawn from these experiments. The 1,2 addition, retro-1,2 addition, 1,4 addition, and retro-1,4 addition of lithiophenylacetonitrile to benzylideneacetone were examined, and a free energy level diagram was constructed for the reaction.
1,2- Vs 1,4-Regioselectivity of Lithiated Phenylacetonitrile toward α,βUnsaturated Carbonyl Compounds. 2. Relation between the Regioselectivity and the Structure of the Species in Solution
Strzalko, Tekla,Seyden-Penne, Jacqueline,Wartski, Lya,Corset, Jacques,Castella-Ventura, Martine,Froment, Francoise
, p. 3295 - 3301 (2007/10/03)
In THF and THF-toluene media, the reaction of lithiated phenylacetonitrile (1) with benzylide-neacetone (5), at low temperature, led to the same ratio of 1,2- and 1,4-adducts after 5 or 30 min of reaction time. The concentrations of the monomeric bridged ion pair 2 preferentially formed in THF and of the dimer of ion pairs 4 predominating in media that favor association such as THF-toluene solvent mixtures were measured from the IR-integrated intensities of the v (C≡N) bands. These concentrations were quantitatively related to the concentrations of the 1,2- and 1,4-adducts, respectively. All these results evidence the kinetic control of this reaction. Intermediate complexes that take into account the peculiar geometries of the monomer 2 and the dimer 4 are proposed to interpret the different regioselectivities observed with 5. This study is extended to cyclic α-enones and cinnamaldehyde. Similar trends hold for the former, while cinnamaldehyde always leads to 1,2-addition. The formation of intermediate complexes allows us to rationalize the cinnamaldehyde behavior but is insufficient to explain the 1,4-addition with cyclic α-enones lying in an s-trans conformation.
Effect of aggregation of nitrile anions on the 1,2 versus 1,4 regioselectivity towards benzylideneacetone
Strzalko,Seyden-Penne,Wartski,Froment,Corset
, p. 3935 - 3936 (2007/10/02)
A direct evidence of the influence of aggregation state of lithiated penylacetonitrile 1 on the 1,2 versus 1,4 regioselectivity towards benzylideneacetone 2 was established. Progressive addition of hexane to THF solutions raised the aggregates proportion of 1 as evidenced by IR ν(CN) band and led to an increase of 1,4 adduct. Monomers afforded 1,2 addition in pure THF.
Structural Study and Reactivity of Carbanions in Solution: Phenyl- and 3-Pyridylacetonitriles
Croisat, Denis,Seyden-Penne, Jacqueline,Strzalko, Tekla,Wartski, Lya,Corset, Jacques,Froment, Francoise
, p. 6435 - 6447 (2007/10/02)
From the IR and (13)C NMR spectra of Li- and K-associated anionic species 1A,M formed phenylacetonitrile in THF, it appears that monomeric tight ion pairs and THF-solvated aggregates are in equilibrium at 0.25 M concentration; the 0.025 M THF solution for
CONJUGATE ADDITION IN PHASE TRANSFER CATALYSIS CONDITIONS: REACTIONS OF α ENONES WITH ARYLACETONITRILES
Cossentini, Moncef,Seyden-Penne, Jacqueline
, p. 689 - 696 (2007/10/02)
Conjugate addition of arylacetonitriles 1-3 to α-enones 4-6 can be performed in liquid-liquid PTC conditions (toluene-saturated aqueous K2CO3 solution).The reaction is too slow with isophorone or mesityloxide to be synthetically useful.
Process for the preparation of alpha-pyrones
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, (2008/06/13)
A process for the preparation of tetrahydro-alpha-pyrones comprises preparing the alkyl ester of a 5-oxo alkanoic acid from a 4-oxo alkane carbonitrile, obtained in a first stage by the action of benzyl cyanide on the corresponding alkenone, and then saponifying the obtained ester, followed by hydrogenation and cyclization.
