- Cu/Ni-doped sulfated zirconium oxide immobilized on CdFe2O4 NPs: a cheap, sustainable and magnetically recyclable inorgano-catalyst for the efficient preparation of α-aminonitriles in aqueous media
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Abstract: A new multifunctional bimetallic nanocatalyst was prepared by immobilization of Cu/Ni-doped sulfated zirconium oxide on magnetic cadmium ferrite (CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni) and used as an efficient recyclable catalyst for one-pot as well as stepwise preparation of α-aminonitriles under mild conditions. The magnetic nanocatalyst was characterized by FTIR, TGA, VSM, XRD, EDX, FE-SEM, and TEM analyses. Also, the surface acidity of the catalyst was measured by pyridine adsorption assay. The catalyst possesses various active sites which could catalyst a variety of aromatic and aliphatic aldehydes to the corresponding α-amionitriles under moderate to high yields in the presence of aniline. Furthermore, transformation of ketones to the desired α-amionitriles and some bis-aminonitriles was also performed by this method. The catalyst could be readily recovered from the reaction mixture and reused for several times without significant loss of activity. Graphic abstract: A general and efficient method has been developed for transformation of a variety of aliphatic, aromatic aldehydes and ketones to the corresponding α-aminonitriles using a multifunctional recyclable CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni nanocatalyst.[Figure not available: see fulltext.]
- Nasseri, Mohammad Ali,Ramezani-Moghadam, Simin,Kazemnejadi, Milad,Allahresani, Ali
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p. 4233 - 4256
(2020/07/08)
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- Efficient synthesis of α-aminonitriles over homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H), as a reusable acid catalyst
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Abstract: Good to excellent yields of α-aminonitriles are achieved through three-component Strecker reaction of aldehydes or ketones with amines and trimethylsilyl cyanides over homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H). The advantages of this protocol include: simplicity, short reaction time, high yields, ease of product isolation and reusability of the catalyst. Graphical abstract: MSNs-HPZ-SO3H is prepared as an acid catalyst and successfully used for three-component Strecker reaction of aldehydes or ketones with amines and trimethylsilyl cyanides (TMSCN) under solvent-free conditions, a straightforward strategy for the synthesis of α-aminonitriles.[Figure not available: see fulltext.].
- Nasresfahani, Zahra,Kassaee, Mohamad Z.,Eidi, Esmaiel
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p. 1819 - 1825
(2019/04/17)
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- Expeditious and efficient synthesis of Strecker's α-aminonitriles catalyzed by sulfated polyborate
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A straightforward, mild, efficient, and environmentally benign protocol for a three-component Strecker reaction of aldehydes or ketones, amines, and trimethylsilyl cyanide catalyzed by sulfated polyborate has been described to afford α-aminonitriles under solvent-free reaction conditions. The major advantages of the present method are excellent yields, shorter reaction time, simple experimental procedure, easy workup procedure, recyclability of the catalyst, solvent-free reaction conditions and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards.
- Indalkar, Krishna S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
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supporting information
p. 2144 - 2148
(2017/05/10)
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- Magnetic solid sulfonic acid decorated with hydrophobic regulators: A combinatorial and magnetically separable catalyst for the synthesis of α-aminonitriles
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A three-component, Strecker reaction of a series of aldehydes or ketones, amines, and trimethylsilyl cyanide for the synthesis of α-aminonitriles in the presence of a catalytic amount of a magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H under solvent-free conditions have been investigated. This catalyst, with a combination of hydrophobicity and acidity on the Fe3O 4@SiO2 core-shell of the magnetic nanobeads, as well as its water-resistant property, enabled easy mass transfer and catalytic activity in the Strecker reaction. The catalyst was easily separated by an external magnet and the recovered catalyst was reused in 6 successive reaction cycles without any significant loss of activity.
- Mobaraki, Akbar,Movassagh, Barahman,Karimi, Babak
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supporting information
p. 352 - 358
(2014/08/05)
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- Nafion-Fe: A new efficient "green" lewis acid catalyst for the ketonic strecker reaction
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The synthesis of various α-aminonitriles, precursors of α-amino acids has been carried out in moderate to high yields and high purity by the Strecker reaction from ketones, aliphatic/aromatic amines and TMSCN using a new "green" Lewis acid catalyst, Nafion-Fe (iron Nafionate, Fe(III) salt of Nafion-H, a solid polymeric perfluoroalkanesulfonic acid) under conventional thermal as well as microwave conditions. Microwave and solvent-free conditions applied in this method shorten the reaction times, improve the yields and diminishes the formation of side products. Strecker reaction occurs smoothly with secondary aliphatic amines also under these conditions which is not common under conventional conditions.
- Surya Prakash,Bychinskaya, Inessa,Marinez, Eric R.,Mathew, Thomas,Olah, George A.
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p. 303 - 312
(2013/05/09)
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- Sulfated tungstate: A green catalyst for Strecker reaction
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A straightforward, mild, efficient, and general method has been developed for the synthesis of α-aminonitriles via Strecker reaction starting from aldehydes or ketones, amines, and trimethylsilyl cyanide in the presence of sulfated tungstate as a heterogeneous mild solid acid catalyst at room temperature and solvent free condition. The developed method has been successfully applied for the synthesis of a wide range of α-aminonitriles with variable functionality.
- Pathare, Sagar P.,Akamanchi, Krishnacharya G.
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experimental part
p. 871 - 875
(2012/03/08)
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- O-Benzenedisulfonimide and its chiral derivative as Bronsted acids catalysts for one-pot three-component Strecker reaction. Synthetic and mechanistic aspects
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o-Benzenedisulfonimide (OBS) has efficiently catalysed the one-pot three-component reaction of ketones and aromatic amines with trimethylsilyl cyanide (TMSCN) giving the corresponding α-amino nitriles in excellent yields (23 examples; average yield 85%). Reaction conditions were very simple, green and efficient. Theoretical calculations have allowed us to explain the mechanism of this reaction which has been found to take place in two phases; the first consists of the nucleophilic addition of the aniline to the ketone and the subsequent dehydration to an imine; the second one consists of the formal addition of cyanide anion to the protonated imine. OBS acts in all steps of this mechanism. Without an acid catalyst, the reaction mechanism is more simple but barriers are sensibly higher. A chiral derivative of OBS was also used and gave fairly good results.
- Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano,Ghigo, Giovanni
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supporting information; experimental part
p. 4058 - 4068
(2012/06/15)
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- Tetraflic acid (1,1,2,2-Tetrafluoroethanesulfonic acid, HC 2F4SO3H) and gallium tetraflate as effective catalysts in organic synthesis
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Tetraflic acid offers ample acidity for various organic reactions that require high acidity. Its gallium(III) salt is an efficient catalyst under mild condtions for synthetic transformations such as the ketonic Strecker reaction for the synthesis of fluorinated α-amino nitriles and condensation- cyclzation reactions using suitable fluoro ketones and 1,2-disubstituted benzenes for the direct preparation of 5-membered or 6-membered fluorinated heterocycles. Copyright
- Prakash, G. K. Surya,Mathew, Thomas,Panja, Chiradeep,Kulkarni, Aditya,Olah, George A.,Harmer, Mark A.
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p. 2163 - 2171
(2012/11/07)
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- Structure-activity relationship for thiohydantoin androgen receptor antagonists for castration-resistant prostate cancer (CRPC)
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A structure-activity relationship study was carried out on a series of thiohydantoins and their analogues 14 which led to the discovery of 92 (MDV3100) as the clinical candidate for the treatment of hormone refractory prostate cancer.
- Jung, Michael E.,Ouk, Samedy,Yoo, Dongwon,Sawyers, Charles L.,Chen, Charlie,Tran, Chris,Wongvipat, John
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experimental part
p. 2779 - 2796
(2010/09/05)
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- Bronsted acid-catalyzed efficient Strecker reaction of ketones, amines and trimethylsilyl cyanide
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A general method for the one-pot, three-component Strecker reaction of ketones was developed using Bronsted acids as organocatalysts. A series of α-aminonitriles were obtained in good to excellent yields (79-99%). A preliminary extension to a catalytic enantioselective three-component Strecker reaction of ketones (up to 40% ee) is also described.
- Zhang, Guang-Wu,Zheng, Dong-Hua,Nie, Jing,Wang, Teng,Ma, Jun-An
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experimental part
p. 1399 - 1405
(2010/06/19)
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- Lewis base-catalyzed three-component Strecker reaction on water. An efficient manifold for the direct α-cyanoamination of ketones and aldehydes
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The first three-component organocatalyzed Strecker reaction operating on water has been developed. The manifold utilizes ketones (aldehydes) as the starting carbonyl component, aniline as the primary amine, acetyl cyanide as the cyanide source and N,N-dim
- Cruz-Acosta, Fabio,Santos-Exposito, Alicia,De Armas, Pedro,Garcia-Tellado, Fernando
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experimental part
p. 6839 - 6841
(2010/03/25)
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- DIARYLHYDANTOIN COMPOUNDS
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The present invention relates to diarylhydantoin compounds, including diarylthiohydantoins, and methods for syntheszing them and using them in the treatment of hormone refractory prostate cancer.
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Page/Page column 26
(2008/06/13)
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- Multicomponent Strecker reaction under high pressure
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For the first time, uncatalyzed, high-pressure (0.6 GPa) reactions with ketones have proven to be a powerful way to perform the three-component Strecker synthesis of α-amino nitriles in high yields. Two types of double Strecker reactions were achieved, but attempts to perform triple Strecker reactions were unsuccessful.
- Matsumoto, Kiyoshi,Kim, Jong Chul,Iida, Hirokazu,Hamana, Hiroshi,Kumamoto, Koji,Kotsuki, Hiyoshizo,Jenner, Gerard
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p. 1734 - 1753
(2007/10/03)
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- Effect of pressure on the Strecker synthesis of hindered α-aminonitriles from ketones and aromatic amines
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The effect of high pressure is examined in Strecker reactions involving ketones, amines and trimethylsilyl cyanide. This effect is small when moderately hindered reactants are involved. However, in the case of aniline and N-methylaniline, the sensitivity of the reaction to pressure increases with increasing steric bulk of the alkyl groups of the ketone. The results confirm the merit of pressure activation as sterically demanding reactions are subject to higher pressure acceleration than their unhindered analogs.
- Jenner, Gérard,Salem, Ridha Ben,Kim, Jong Chul,Matsumoto, Kiyoshi
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p. 447 - 449
(2007/10/03)
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- High pressure mediated three component Strecker synthesis of α-aminonitriles from ketones, aromatic amines and trimethylsilyl cyanide
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High pressure (600 MPa) reaction conditions, in the absence of a catalyst, have proved to be a powerful way to stimulate the three component Strecker reaction synthesis of α-aminonitriles in high yields. Examples of two types of double Strecker reactions were also described.
- Matsumoto, Kiyoshi,Kim, Jong Chul,Hayashi, Naoto,Jenner, Gérard
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p. 9167 - 9169
(2007/10/03)
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- Synthesis of new imidazolidinones, spiro-imidazolidinones and spiro-hydantoins
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α-Alkyl/aryl-α-arylaminopropionitriles (1) and 1-arylamino-1-cyano-cyclohexanes/cyclopentanes (5) react with alkyl/arylisocyanates to afford new imidazolidinones (2, 3) and spiro-imidazolidinones (6, 7) respectively. Compounds 2 and 6 on hydrolysis give hydantoins (4) and spiro-hydantoins (8), respectively.
- Chande, Madhukar S.,Balel, Satish K.
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p. 377 - 380
(2007/10/03)
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- THERMAL Z,E-ISOMERIZATION OF IMINES. IV. ANILS OF ACETONE
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It has been established by the correlation between the values of log k298 and the ? constants that the degenerate thermal Z,E-isomerization of anils of acetone takes place according to an inversion mechanism, with the exception of acetone p-dimethylaminophenylimine, which isomerizes predominantly according to a rotation mechanism.The increase in the steric stresses upon the introduction of ortho substituents into the aryl ring of anils of acetone results in significant lowering of the barriers to the inversion of the nitrogen atom.The raising of the barriers to inversion in phenylimines as the electron-acceptor properties of the substituents on the imino carbon atom are enhanced is due to the weakening of the n?N-?*Ph interaction as a consequence of the increase in the energy gap between the interacting orbitals as a result of the lowering of the energy of the n?N orbital.
- Prosyanik, A. V.,Kol'tsov, N. Yu.,Romanchenko, V. A.
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p. 1330 - 1337
(2007/10/02)
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