- Application of various types of alumina and nano-γ- Alumina sulfuric acid in the synthesis of α-aminonitriles derivatives: Comparative study
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An efficient and green protocol for the synthesis of α-aminonitrile derivatives by one-pot reaction of different aldehydes with amines and trimethylsilyl cyanide has been developed using natural alumina, alumina sulfuric acid (ASA), nano-γ-alumina, nano-γ
- Teimouri, Abbas,Ghorbanian, Leila,Moatari, Athar
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Read Online
- Three helical chain-based 3D coordination polymers: Solvent-induced syntheses, tunable structures and catalytic properties for the Strecker reaction
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Three three-dimensional (3D) helical chain-based coordination polymers [Sc(aip)(OH)·(H2O)]n (1), [Sc2(aip)3]n (2) and [Sc2(nip)3]n (3) (H2aip = 5-aminoisoph
- Chai, Juan,Zhang, Ping,Shi, Xiangxiang,Sun, Jing,Wang, Li,Fan, Yong
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Read Online
- Catalytic Strecker reaction: g-C3N4-anchored sulfonic acid organocatalyst for the synthesis of α-aminonitriles
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Abstract: Efficient organocatalyst for enantioselective Strecker reaction was synthesized using g-C3N4 sheets (CN). CN-anchored sulfonic acid (CN-Bu-SO3H) was found to be a highly efficient and recoverable organocatalyst f
- Rahmati, Monavar,Ghafuri, Hossein
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p. 1489 - 1502
(2021/02/16)
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- Synthesis and characterization of Pd supported on methane diamine (propyl silane) functionalized Fe3O4 nanoparticles as a magnetic catalyst for synthesis of α-aminonitriles and 2-methoxy-2-phenylacetonitrile derivative via Strecker-t
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Pd supported on methane diamine (propyl silane) functionalized Fe3O4 magnetic nanoparticles as an organic–inorganic hybrid heterogeneous catalyst was fabricated and characterized by FT-IR, XRD, SEM, TEM, TGA, VSM, EDX, and ICP-AES te
- Li, Qun,Liu, Wei,Mohammadnia, Majid,Song, Di,Sun, Mingzhe,Wu, Wei,Yan, Li
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- A carbon dioxide-promoted three-component Strecker reaction
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A three-component Strecker reaction of aldehydes, amines and KCN has been performed for the first time in supercritical carbon dioxide. In the proposed procedure, non-toxic and non-flammable carbon dioxide acts not only as an environmentally benign reaction medium but also as a reaction promoter via in situ formation of carbonic acid which provides a gradual release of the true cyanating agent (HCN) from available KCN. The reaction conditions (pressure, temperature, and concentrations of reagents) were optimized, and various aromatic and aliphatic amines and aldehydes were transformed into valuable α-amino nitriles including prospective pharmacological substances. The equimolar amount of used cyanogen reagent, carrying out the process in a sealed autoclave in a 'green' solvent medium under mild conditions (90 bar, 35 °C) along with the high yields of products and the scalability of the developed procedure make it suitable for sustainable industrial applications. This journal is
- Fauziev, Ruslan V.,Ivanov, Roman E.,Kuchurov, Ilya V.,Zlotin, Sergei G.
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p. 10137 - 10144
(2021/12/24)
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- KF/clinoptilolite nanoparticles as an efficient nanocatalyst for the Strecker synthesis of α-aminonitriles
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Abstract: Potassium fluoride impregnated on clinoptilolite nanoparticles (KF/CP NPs) have been explored to serve as an effective and inexpensive heterogeneous catalyst for the one-pot three-component Strecker synthesis of a variety of α-aminonitriles at room temperature in ethanol as a green solvent. KF/CP NPs have been synthesized using simple impregnation techniques in aqueous media from readily available inexpensive starting materials and displayed its initial catalytic activity even after five runs. The easy preparation and separation of catalyst, simple procedure, mild reaction conditions, and excellent yields of products render this method as an attractive sustainable option. Graphic abstract: [Figure not available: see fulltext.]
- Khalilzadeh, Mohammad A.,Oladee, Razieh,Zareyee, Daryoush
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- Targeted development of hydrophilic porous polysulfonamide gels with catalytic activity
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We report the use of a template and functional monomers in the synthesis of three novel polysulfonamide gels with new architectures and functional groups. These mesoporous polysulfonamide gels were prepared by the condensation polymerization of benzene-1,3-disulfonyl chloride (as the main precursor), linear monomers, and cross-linkers (as variable precursors) in the presence of a silica template by a combination of sol-gel chemistry and the nanocasting technique. In this synthesis pathway, in situ polymerization onto the template surface led to the construction of a silica/polymer nanocomposite. Next, after removal of the template, the nanocomposite gels were transformed into mesoporous polysulfonamide nanospheres. After the physicochemical identification of the synthesized materials, functionalized polysulfonamides were used as reusable novel catalysts with high efficiency for the Strecker reaction under mild conditions. These polymers have Br?nsted/Lewis acid active sites, a mesoporous structure, and hydrogen bonding. Moreover, since these polymers are hydrogels that can absorb water, they can promote the Strecker reaction through chemical absorption of the generated water as a driving force. Overall, this article describes a novel synthesis procedure and application of porous polysulfonamide gels.
- Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin
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- Phosphine-Catalyzed Sequential Michael Addition between α-Aminonitriles and Methyl Acrylate for Cyclization: Synthesis of N-Aryl-Substituted Pyrrolidines
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Abstract: N-Aryl-substituted pyrrolidine derivativeswere synthesized via tributylphosphine-catalyzed sequential Michael addition ofα-aminonitriles and methyl acrylate as starting materials. The first Michaeladdition between α-aminonitrile and methyl acryl
- Jang,Sin,Paek,Jang,Jong
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p. 2228 - 2235
(2021/02/09)
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- Radical Rearrangement of Aryl/Alkylidene Malononitriles via Aza Michael Addition/Decynoformylation/Addition Sequence: An Access to α-Aminonitriles and α-Aminoamides
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An efficient, safe, and environmentally friendly tertiary butyl hydrogen peroxide (TBHP)-mediated rearrangement of aryl/alkylidene malononitrile with anilines has been developed with in situ generation of HCN as the cyanide source for the synthesis of sub
- Bhoite, Shubhangi P.,Bansode, Ajay H.,Suryavanshi, Gurunath
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p. 14858 - 14865
(2020/12/02)
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- Fe3O4?SiO2 nanoparticles–functionalized Cu(II) Schiff base complex with an imidazolium moiety as an efficient and eco-friendly bifunctional magnetically recoverable catalyst for the Strecker synthesis in aqueous media at room temperature
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Cu(II) Schiff base complex supported on Fe3O4?SiO2 nanoparticles was employed as a magnetic nanocatalyst (nanocomposite) with a phase transfer functionality for the one-pot preparation of α-aminonitriles (Strecker reaction). The desired α-aminonitriles were obtained from the reaction of aromatic or aliphatic aldehydes, aniline or benzyl amine, NaCN, and 1.6 mol% of the catalyst in water at room temperature and good to excellent yields were obtained for all substrates. The catalyst was characterized analytically and instrumentally including Fourier-transform infrared spectroscopy, X-ray diffraction, thermogravimetric, nuclear magnetic resonance, energy-dispersive X-ray spectroscopy, inductively coupled plasma spectroscopy, vibrating-sample magnetometry analysis, dynamic light scattering, Brunauer–Emmett–Teller surface area, field emission scanning electron microscopy, and transmission electron microscopy analyses. The reaction mechanism was investigated, in which the performance of the catalyst as a phase transition factor seems to be probable. The catalyst showed high activity, high turnover frequency (TOF)s, significant selectivity, and fast performance toward the Strecker synthesis. The nanocatalyst can be readily and quickly separated from the reaction mixture with an external magnet and can be reused for at least seven successive reaction cycles without significant reduction in efficiency.
- Kazemnejadi, Milad,Alavi G., Seyyedeh Ameneh,Rezazadeh, Zinat,Nasseri, Mohammad Ali,Allahresani, Ali,Esmaeilpour, Mohsen
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- Transition Metal Ions Regulated Structural and Catalytic Behaviors of Coordination Polymers
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Three new coordination polymers (CPs), I [Cu(L)(H2O)]·2H2O, II [Zn(L)], and III [Ag(HL)(CH3CN)], were synthesized by employing a novel pyrazole-based dicarboxylate ligand (H2L) through a solvothermal strategy. Single-crystal structural analysis established that compounds I and II exhibit two-dimensional (2D) sheet structures, while compound III possesses a one-dimensional (1D) ladder structure due to the connectivity of terminal solvent moiety. The geometries of metal ions vary from square planar (Cu2+ ion) to distorted tetrahedral (Zn2+ and Ag+ ion). Topological study showed that compound I has made a (4·62)2(42·62·82) net, while compounds II and III have exposed common (44·62) SQL net and (42·6) net, respectively. The Lewis acidic nature of compounds I, II, and III has been confirmed with various heterogeneous catalytic reactions. For the first time, one-pot multicomponent synthesis of α-amino amidine has been performed by the three CPs and the reaction kinetics has been altered by the variation of Lewis acidic metal centers. The roles of metal ions for structural variations and the catalytic performances are investigated in a series of CPs.
- Kumar, Nikhil,Rom, Tanmay,Singh, Virender,Paul, Avijit Kumar
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p. 5277 - 5288
(2020/09/09)
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- Gallic acid-functionalized magnetic nanoparticles: a convenient and green approach for synthesis of α-aminonitriles under solvent-free conditions
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Abstract: Gallic acid-coated magnetic nanoparticles were efficiently prepared, characterized by Fourier transform infrared spectroscopy, X-ray diffraction, vibrating sample magnetometry, scanning electron microscopy, and transmission electron microscopy, and employed as an environmentally friendly and recyclable catalyst for one-pot synthesis of three-component reaction via Strecker reaction, incorporating aldehydes/ketones, amines, and trimethylsilyl cyanides under solvent-free conditions. Operational simplicity, product purity, natural resources and reusability of the catalyst are considered as evident features of this protocol which will hopefully develop into an inexpensive, efficient, and clean strategy for the synthesis of α-aminonitriles. Graphical abstract: [Figure not available: see fulltext.].
- Eidi, Esmaiel,Kassaee, Mohamad Z.,Nasresfahani, Zahra,Cummings, Peter T.
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p. 303 - 314
(2018/10/15)
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- Gallic acid grafted to amine-functionalized magnetic nanoparticles as a proficient catalyst for environmentally friendly synthesis of α-aminonitriles
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An effective approach of one-pot catalytic Strecker reaction between aromatic aldehydes, aniline or toluidine and trimethylsilyl cyanide in the presence of amine-functionalized Fe3O4@SiO2 nanoparticles grafted with gallic
- Maleki, Ali,Azadegan, Sepide,Rahimi, Jamal
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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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- Synthesis and characterization of an acidic nanostructure based on magnetic polyvinyl alcohol as an efficient heterogeneous nanocatalyst for the synthesis of α-aminonitriles
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The present study described design, preparation and characterization of a new magnetic nanocomposite based on polyvinyl alcohol (PVA) as a non-toxic, water-soluble, high mechanical stable and low-cost polymer. Fourier transform infrared (FT-IR) spectroscopy, field-emission scanning electron microscopy (FE-SEM) image, transmission electron microscope (TEM) image, X-ray diffraction (XRD) pattern, energy-dispersive X-ray (EDX) analysis and thermogravimetric (TG) analysis were used to describe the morphological, chemical and physical properties of the prepared nanocatalyst. All these results confirmed the successful synthesis of Fe3O4@PVA-SO3H. This heterogeneous nanocatalyst was then successfully used for the synthesis of α-aminonitrile derivatives by starting from an aldehyde, an aniline and trimethylsilyl cyanide (TMSCN). High efficiency, green chemistry properties, simple and easy separation are the specific properties of this nanocomposite. Fe3O4@PVA-SO3H can be derived out by an external magnet and reused ten times without any changes in its structure.
- Maleki, Ali,Rahimi, Jamal,Hajizadeh, Zoleikha,Niksefat, Maryam
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- Synthesis of 1-(α-aminoalkyl)-2-naphthol and α-aminonitrile derivatives with molybdenum Schiff base complex covalently bonded on silica-coated magnetic nanoparticles and DNA interaction study of one type of derivatives using computational and spectroscopi
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An air- and moisture-stable molybdenum Schiff base complexes immobilized on magnetic iron oxide nanoparticles with a core-shell structure was developed for utilization as a new heterogeneous catalyst. The surface, structural and magnetic characteristics o
- Rakhtshah, Jamshid,Shaabani, Behrouz,Salehzadeh, Sadegh,Hosseinpour Moghadam, Neda
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p. 420 - 430
(2019/01/23)
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- A Facile Approach to Catalyst-Free Cyanation and Azidation of a-Organic Compounds and a One-Pot Preparation of 5-Substituted 1 H-Tetrazoles by Using a Dimethyl Sulfoxide-Nitric Acid Combination
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In this study, cyanations or azidations of imines were performed by using hydroxy(dimethyl)-λ 4-sulfanecarbonitrile or azido(dimethyl)-λ 4-sulfanol, respectively, prepared in situ by treatment of potassium cyanide or sodium azide with a dimethyl sulfoxide-nitric acid combination. Furthermore, a one-pot preparation of 5-substituted 1 H-tetrazole derivatives was carried out by using this reagent combination in the presence of an aldehyde, hydroxylamine hydrochloride, and sodium azide under mild conditions.
- Alavi, Seyyedeh Ameneh,Kazemnejadi, Milad,Mahmoudi, Boshra,Nasseri, Mohammad Ali
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p. 2290 - 2294
(2019/12/11)
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- Synthesis of α-Aminonitriles and 5-Substituted 1H-Tetrazoles Using an Efficient Nanocatalyst of Fe3O4@SiO2–APTES-supported Trifluoroacetic Acid
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Fe3O4@SiO2–APTES-supported trifluoroacetic acid nanocatalyst was used for the one-pot synthesis of α-aminonitriles via a three-component reaction of aldehydes (or ketones), amines, and sodium cyanide. This method produced a high yield of 75–96% using only a small amount of the catalyst (0.05?g) in EtOH at room temperature. The catalyst was also employed for the synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide in EtOH at 80°C. The tetrazoles were produced with good-to-excellent yields in a short reaction time of 4?h. Both synthetic methods were carried out in the absence of an organic volatile solvent. Because the supported trifluoroacetic acid generated a solid acid on the surface, thus the acid corrosiveness was not a serious challenge. This heterogeneous nanocatalyst was magnetically recovered and reused several times without significant loss of catalytic activity.
- Fatahi, Hosna,Jafarzadeh, Mohammad,Pourmanouchehri, Zahra
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p. 2090 - 2098
(2019/07/05)
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- A unique combination of KI/ZnFe2O4 as a catalyst for oxidative Strecker reaction
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α-Aminonitriles as key intermediates for the preparation of α-amino acid derivatives, amides, diamines, peptides, proteins and heterocycles were synthesized through methylarene oxidation in the Strecker reaction using a unique combination of KI/ZnFe2O4 as the best catalyst and aqueous tert-butyl hydroperoxide as oxidant. A wide range of amines and methylarenes were converted to the corresponding products. Operational simplicity, short reaction time and recyclability of the catalyst are advantages of this protocol.
- Ghandi, Leila,Kazemi Miraki, Maryam,Karimi, Meghdad,Radfar, Iman,Heydari, Akbar
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- A N - aryl methylaniline of α - carbonitriding method
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A N - aryl methylaniline of α - carbonitriding method. This law to various N - aryl aniline derivatives as raw materials, trimethylsilyl cyanide as the cyanide reagent, 2, 3 - dichloro - 5, 6 - dicyano - 1, 4 - benzoquinone as oxidizing agent in a solvent reaction after concentration, purification of a simple process to get the finished product. The purpose is for the existing N - aryl aniline oxidation carbonitriding method of deficiencies, provide a new synthesis method. The method adopts the low price, low toxicity, and easily obtained 2, 3 - dichloro - 5, 6 - dicyano - 1, 4 - benzoquinone as the oxidizing agent, the non-metal ion catalysis, high-efficiently the various N - aryl methylaniline with three oxidation of trimethylsilyl cyanide. The method of the invention the process is simple, preparing the reaction production safety, easy operation, reaction time is short, favorable to the industrialized.
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Paragraph 0155-0159
(2019/07/04)
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- A Metal-Organic Framework to CuO Nanospheres of Uniform Morphology for the Synthesis of α-Aminonitriles under Solvent-Free Condition along with Crystal Structure of the Framework
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Herein, we have reported the synthesis, crystal structure, thermogravimetric property, and photoluminescence activity of a new Cu-based metal organic framework (MOF): {[Cu2(2,5-pdc)2(ald-4)(H2O)2]·3H2
- Singha, Soumen,Saha, Arijit,Goswami, Somen,Dey, Sanjoy Kumar,Payra, Soumen,Banerjee, Subhash,Kumar, Sanjay,Saha, Rajat
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p. 189 - 199
(2018/01/12)
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- Three-component solventless Strecker synthesis of α-aminonitriles catalysed by a renewable sulfonated nanoporous carbon catalyst (CMK-5-SO3H)
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The one-pot three-component synthesis of a variety of α-aminonitriles has been studied using a catalytic amount of a sulfonic acid-functionalized ordered nanoporous carbon catalyst, CMK-5-SO3H, at room temperature under solvent-free reaction co
- Zareyee, Daryoush,Rad, Ali Shokuhi,Ataei, Zahra,Javadi, Sayed Hossein,Khalilzadeh, Mohammad A.
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- Fe3O4/MIL-101(Fe) nanocomposite as an efficient and recyclable catalyst for Strecker reaction
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A highly porous metal-organic framework, MIL-101(Fe), was prepared by a solvothermal method in the presence of amino-modified Fe3O4@SiO2 nanoparticles, in order to achieve Fe3O4/MIL-101(Fe) nanocomposite, which was characterized by XRD, FT-IR, SEM, TEM, BET, and VSM. This hybrid magnetic nanocomposite was employed as heterogeneous catalyst for α-amino nitriles synthesis through three-component condensation reaction of aldehydes (ketones), amines, and trimethylsilyl cyanide in EtOH, at room temperature. The recoverability and reusability was admitted for the heterogeneous magnetic catalyst; no significant reduction of catalytic activity was observed even after five consecutive reaction cycles.
- Mostafavi, Mohammad Mahdi,Movahedi, Farnaz
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- An in-based 3D metal-organic framework as heterogeneous Lewis acid catalyst for multi-component Strecker reactions
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A novel three-dimensional metal-organic framework (MOF) {[In3(NIPH)3 (HNIPH)(OH)2]·4H2O}n (1) (H2NIPH = 5-nitroisophthalic acid) with one-dimensional channels was synthesized and structurally characterized. Importantly, it demonstrates excellent catalytic activity for the Strecker reactions of two or three components under mild conditions. Moreover, the catalytic recycling of 1 as a representative example was explored. It can be easily separated and reused for no less than five runs with more than 80% conversion yield in catalytic ability.
- Chai, Juan,Zhang, Ping,Xu, Jianing,Qi, Hui,Sun, Jing,Jing, Shubo,Chen, Xiaodong,Fan, Yong,Wang, Li
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p. 165 - 171
(2018/05/07)
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- Copper-vitamin B6 coated on maghemite nanoparticles: A new convenient dual catalysis system to synthesize α-aminonitriles from benzyl alcohols
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A novel and effective dual catalysis system, copper combined with pyridoxal phosphate, which is anchored in maghemite nanoparticles were designed and applied to synthesize α-aminonitriles from benzyl alcohols. This catalytic system has the potential ability to perform oxidation reactions and subsequently synthesize alpha-amino nitrile in a reaction environment. Thus, the purpose of this paper is introducing a heterogeneous, sustainable and recyclable catalytic system to perform reactions that require a transition metal catalyst and organocatalyst continuously to achieve a target molecule. The catalysis system is examined and investigated with seven useful analyses such as FT-IR, TGA, VSM, SEM, TEM, XRD, and ICP.
- Esfandiary, Naghmeh,Nakisa, Athar,Radfar, Iman,Azizi, Kobra,Mehraban, Jamshid Azarnia,Heydari, Akbar
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- Cross-dehydrogenative coupling strategy for phosphonation and cyanation of secondary N-alkyl anilines by employing 2,3-dichloro-5,6-dicyanobenzoquinone
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The cross-dehydrogenative coupling strategy for metal-free phosphonation and cyanation of secondary N-alkyl anilines has been developed firstly under mild reaction conditions. Based on detailed optimization of reaction conditions, the substrate generality of N-alkyl anilines and various hydrogen phosphonates has been investigated, and a series of versatile α-aminophosphonates and α-aminonitriles were therefore furnished in good to excellent yields. A plausible collective reaction mechanism through dehydrogenation to imine formation, then to respective α-aminophosphonates and α-aminonitriles was proposed.
- Liu, Qing,Yu, Shuchen,Hu, Liangzhen,Hussain, Muhamad Ijaz,Zhang, Xiaohui,Xiong, Yan
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p. 7209 - 7217
(2018/11/10)
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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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- A catalytic, one-pot and green synthesis of a-amino nitriles: Cu(BF4)2.x H2O an efficient catalyst
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The Strecker reaction is a first reported multicomponent reaction for the preparation of a-aminonitriles. The a-aminonitriles are important intermediates for various aminoacids, 1,2-diazines, heterocycles and biologically active compounds like Saframycin A and Ecteinascidin 746. The preparation of a-aminonitriles by Strecker approach using MCR attracted many research groups owing atom economy to avoid multistep synthesis and to follow Green chemistry principles. Methods: A-aminonitriles have been synthesized using Strecker reaction by treatment of aldehydes, amines, with TMSCN in the presence of Cu(BF4)2.xH2O as a catalyst in one pot under neat conditions. Various aromatic and aliphatic aldehydes have been studied with different primary and secondary amines. Results: The reaction condition has been optimized by choosing a model reaction under various solvents and found good yields under neat conditions. Moreover, various catalytic amounts of Cu(BF4)2.xH2O has also been studied and found 3 mole% providing better yields. The reaction has been studied with different substrates of aldehydes and amines. Some of the products were characterized by comparison of their spectral data (1H NMR, 13C NMR, IR and MS) and physical properties with those of authentic samples reported in the literature. Conclusion: Afacile and efficient one-pot synthesis of a-amino nitriles at ambient temperature using copper(II)tetrafluoroborate as a novel catalyst under solvent-free conditions via Strecker reaction is reported. The process is simple and environmentally benign using the commercially available and inexpensive catalyst.
- Tadiparthi, Krishnaji,Raghavendra,Kamal, Ahmed
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supporting information
p. 440 - 445
(2017/07/24)
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- Molybdenum Schiff base complex supported on MNPs as an efficient and easily recyclable catalyst in three-component Strecker reaction for synthesis of α-aminonitrile derivatives
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Abstract: An efficient and straight procedure has been described for one-pot multi-component synthesis of α-aminonitrile derivatives in the presence of a molybdenum Schiff base complex supported on magnetite nanoparticles as a heterogeneous catalyst. The
- Rakhtshah, Jamshid,Salehzadeh, Sadegh
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p. 6973 - 6991
(2017/10/06)
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- Highly efficient three-component Strecker-type reaction catalyzed by MgI2 etherate under solvent-free conditions
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A concise, straightforward and efficient method has been developed for the synthesis of α-aminonitriles by an one-pot three-component condensation of aldehydes or ketones, amines and trimethylsilyl cyanide catalyzed by MgI2 etherate under solvent-free conditions. This protocol has some advantages such as mild reaction condition, simple work-up, short reaction time and high product yields.
- Li, Pengcheng,Zhang, Yongdong,Chen, Zhili,Zhang, Xingxian
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supporting information
p. 1854 - 1858
(2017/04/21)
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- Design, synthesis, characterization and catalytic performance of a new cellulose-based magnetic nanocomposite in the one-pot three-component synthesis of α-aminonitriles
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A sulfonated magnetic cellulose-based nanocomposite was prepared and characterized using scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction and Fourier transform infrared spectroscopy. Then, it was used as a green nanoca
- Maleki, Ali,Akhlaghi, Elnaz,Paydar, Reza
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p. 382 - 386
(2016/05/19)
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- Magnetic Fe3O4-BF3: Highly efficient Lewis acid catalyst for the synthesis of α-aminonitriles
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Fe3O4 magnetic nanoparticle-supported BF3 was prepared as a new magnetically separable Lewis acid catalyst and successfully used for the one-pot synthesis of α-aminonitriles. A broad range of substrates including the aromatic and heteroaromatic aldehydes, cyclic ketones (cyclopentanone, cyclohexanone and cycloheptanone), aryl-alkyl ketones, diaryl ketones and tetralones, isatin derivatives and acenaphthenequinone were condensed with amines (aliphatic and aromatic) and trimethylsilyl cyanide. All reactions were completed in short times and products were obtained in good to excellent yields. The catalyst could be recycled and reused several times without any loss of efficiency. Finally, α-aminonitrile containing adenine was successfully synthesized.
- Shekouhy, Mohsen,Moaddeli, Ali,Khalafi-Nezhad, Ali
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p. 3805 - 3827
(2016/04/05)
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- Design and development of a novel cellulose/γ-Fe2O3/Ag nanocomposite: A potential green catalyst and antibacterial agent
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A cellulose/γ-Fe2O3/Ag nanocomposite is synthesized and used as a catalyst for the synthesis of trisubstituted imidazoles and α-aminonitriles. This catalytic protocol is simple, the reaction yield is very high, and the reaction time is very short. The remarkable magnetic properties of the nanocomposite permit easy separation of the catalyst from the reaction mixture without considerable loss of catalytic activity. In addition, antibacterial properties of the nanocomposite are investigated. For this purpose, S. aureus as the representative of Gram-positive bacteria and E. coli as the representative of Gram-negative bacteria are evaluated. To study the morphology and characterization of the prepared nanocomposite, X-ray diffraction patterns (XRD), energy-dispersive X-ray spectroscopy (EDX), field-emission scanning electron microscopy (FE-SEM), vibrating sample magnetometry (VSM) and thermal gravimetric analysis/differential thermal analysis (TGA/DTA) are obtained.
- Maleki, Ali,Movahed, Hamed,Paydar, Reza
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p. 13657 - 13665
(2016/02/18)
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- Role of (3-aminopropyl)tri alkoxysilanes in grafting of chlorosulphonic acid immobilized magnetic nanoparticles and their application as heterogeneous catalysts for the green synthesis of α-aminonitriles
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The surface modification of SiO2 coated Fe3O4 nanoparticles by grafting silane coupling agents is a highly significant approach to enhancing the interface interaction between the inorganic magnetic core and the organic fun
- Singh, Harminder,Rajput, Jaspreet Kaur,Arora, Priya,Jigyasa
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p. 84658 - 84671
(2016/10/31)
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- A fast and benign synthesis of α-aminonitriles by reusable immobilized AlCl3on γ-Al2O3
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Reusable, immobilized AlCl3 on γ-Al2O3 is generated by the reaction of AlCl3 on activated γ-Al2O3 of 58 A at 600°C. This is an efficient, catalytic, safe and environmentally acceptable catalyst for the synthesis of a series of α-aminonitriles utilizing Strecker's process by the reaction of carbonyl compounds, amines and trimethylsilyl cyanide (TMSCN) with excellent yields at ambient temperature. The catalyst can be easily recycled and has been reused for thirteen runs without losing its activity.
- Pamar, M. Geeta,Govender,Pillay,Abrahamse,Nanjundaswamy
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p. 110 - 116
(2015/01/30)
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- Nano magnetic sulfated zirconia (Fe3O4@ZrO2/SO42-): An efficient solid acid catalyst for the green synthesis of α-aminonitriles and imines
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In this research, nano magnetic sulfated zirconia was prepared and characterized by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD) measurements and vibrational sample magnetometry (VSM). Its catalytic activity was investigated for the one-pot three component green synthesis of α-aminonitriles using various aldehydes and ketones at room temperature in ethanol. This protocol has various advantages such as: simple work-up, short reaction time, high product yields and easy recovery and reusability of the catalyst.
- Ghafuri, Hossein,Rashidizadeh, Afsaneh,Ghorbani, Behnaz,Talebi, Majid
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p. 4821 - 4829
(2015/06/16)
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- Aqueous formic acid: An efficient, inexpensive and environmentally friendly organocatalyst for three-component Strecker synthesis of α-aminonitriles and imines with excellent yields
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Aqueous formic acid (37%) which is an efficient, inexpensive and environmentally friendly organocatalyst was used in the Strecker reaction to afford α-aminonitriles and imines. Reaction was carried out under mild conditions and room temperature in high yi
- Ghafuri, Hossein,Roshani, Mahdi
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p. 58280 - 58286
(2015/02/19)
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- Strong Lewis acid air-stable cationic titanocene perfluoroalkyl(aryl) sulfonate complexes as highly efficient and recyclable catalysts for C-C bond forming reactions
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A series of strong Lewis acid air-stable titanocene perfluoroalkyl(aryl) sulfonate complexes Cp2Ti(OH2)2(OSO 2X)2·THF (X = C8F17, 1·THF; X = C4F9, 2·H2O· THF; X = C6F5, 3) were successfully synthesized by the treatment of Cp2TiCl2 with C8F 17SO3Ag, C4F9SO3Ag and C6F5SO3Ag, respectively. In contrast to well-known titanocene bis(triflate), these complexes showed no change in open air over three months. TG-DSC analysis showed that 1·THF, 2·H 2O·THF and 3 were thermally stable at 230 °C, 220°C and 280°C, respectively. Conductivity measurements showed that these complexes underwent ionic dissociation in CH3CN solution. X-ray analysis results confirmed that 2·H2O·THF and 3 were cationic. ESR spectra showed that the Lewis acidity of 1·THF (1.06 eV) was higher than that of Sc3+ (1.00 eV) and Y3+ (0.85 eV). UV/Vis spectra showed a significant red shift due to the strong complex formation between 10-methylacridone and 2·H2O·THF. Fluorescence spectra showed that the Lewis acidity of 2 (λem = 477 nm) was higher than that of Sc3+ (λem = 474 nm). These complexes showed high catalytic ability in various carbon-carbon bond forming reactions. Moreover, they show good reusability. Compared with 1·THF, 2·H2O·THF and 3 exhibit higher solubility and better catalytic activity, and will find broad applications in organic synthesis. This journal is the Partner Organisations 2014.
- Li, Ningbo,Wang, Jinying,Zhang, Xiaohong,Qiu, Renhua,Wang, Xie,Chen, Jinyang,Yin, Shuang-Feng,Xu, Xinhua
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supporting information
p. 11696 - 11708
(2014/07/22)
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- Zn(OAc)2·2H2O-catalyzed one-pot efficient synthesis of α-amino nitriles
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A mild, efficient one-pot three component strecker reaction involving electronically and structurally divergent aldehydes, amines and trimethly silyl cyanide in chloroform as solvent at room temperature was accomplished in moderate to excellent yields using an inexpensive and readily available catalyst, Zn(OAc)2.2H2O.
- Reddy, V. Venkata Rami,Saritha,Ramu,Varala, Ravi,Jayashree
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p. 7439 - 7442
(2015/04/22)
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- Glycerol mediated strecker reaction: Catalyst-free protocol for the synthesis of α-amino nitriles
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Environmental friendly multicomponent protocol for the preparation of α-amino nitriles has been developed. In this methodology, glycerol was demonstrated as an efficient and alternative solvent for organic synthesis. After the reaction, glycerol was recov
- Ghogare, Ramesh S.,Rajeshwari,Narsaiah, A. Venkat
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supporting information
p. 688 - 692
(2015/04/14)
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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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- Efficient three-component Strecker reaction of acetals and aromatic amines catalysed by hafnium tetrachloride at room temperature
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A straightforward, mild, efficient, one-pot method has been found for the synthesis of á-aminonitriles via three-component Strecker reaction using acetals or cyclic acetals, curious aromatic amines and trimethylsilyl cyanide (TMSCN) catalysed by hafnium tetrachloride at room temperature. It is with good to excellent yields under mild conditions. This developed approach has been successfully applied for the synthesis of a wild rang of á-aminonitriles with a variety of functional groups.
- Zhang, Xue-Lin,Wu, Qin-Pei,Zhang, Qing-Shan
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p. 690 - 693
(2014/01/17)
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- Silica boron sulfuric acid nanoparticles: As an efficient and reusable catalyst for the large-scale synthesis of α-amino nitriles using the strecker reaction
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A highly efficient and green procedure for the large-scale synthesis of α-amino nitriles using three-component condensation of carbonyl compounds, amines, and trimethylsilylcyanide has been developed. Silica boron sulfuric acid nanoparticles (SBSANs) are found as an efficient heterogeneous catalyst for the promotion of this process at room temperature under solvent-free conditions. This protocol offers an effective and scale-up procedure for the synthesis of various α-amino nitriles using a wide range of amines and carbonyl compounds in relatively short reaction time with the excellent isolated yields. In addition, the SBSAN catalyst is easily separated from the reaction mixture by simple filtration and can be reused several times.
- Khalafi-Nezhad, Ali,Foroughi, Habib Ollah,Panahi, Farhad
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- Chitosan: A highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions
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Commercial chitosan-without any post-modification with active Bronsted or Lewis acid centers-was found to be a highly efficient renewable and recoverable bio-polymer catalyst for the rapid and convenient synthesis of α-amino nitriles or imines from aromatic aldehydes and amines under mild reaction conditions at room temperature in high to quantitative yields. The α-amino nitrile derivatives were prepared through the Strecker reaction using trimethylsilyl cyanide (TMSCN) and catalyzed by chitosan as a heterogeneous bifunctional organocatalyst.
- Dekamin, Mohammad G.,Azimoshan, Mojtaba,Ramezani, Leila
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supporting information
p. 811 - 820
(2013/04/10)
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- Dehydroascorbic acid (DHAA) capped magnetite nanoparticles as an efficient magnetic organocatalyst for the one-pot synthesis of α-aminonitriles and α-aminophosphonates This article is dedicated to memory of Majid Shahriari
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A dehydroascorbic acid capped magnetite (DHAA-Fe3O4) catalyst is prepared and used for the one-pot synthesis of α-aminonitriles and α-aminophosphonates. Different derivatives of these compounds are synthesized in good yields.
- Saberi, Dariush,Cheraghi, Samaneh,Mahdudi, Samaneh,Akbari, Jafar,Heydari, Akbar
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p. 6403 - 6406
(2013/11/19)
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- A novel approach to the synthesis of α-aminonitriles using triphenyl-phosphine dibromide under solvent-free conditions
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A quick and highly efficient, one-pot, three-component, solvent-free method for the synthesis of α-aminonitriles starting from the corresponding carbonyl compounds, amines, and trimethylisocyanide using triphenylphosphine dibromide, has been developed. Diverse α-aminonitriles have been synthesized in good to excellent yields (80-99%) using a range of aldehydes, ketones and amines. Georg Thieme Verlag Stuttgart · New York.
- Chaturvedi, Devdutt,Chaturvedi, Amit K.,Dwivedi, Parmesh K.,Mishra, Nisha
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- Zinc triflate a water compatible, green catalyst in one pot three-component efficient synthesis of α-Amino nitriles
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α-Amino nitriles are synthesized in one pot three-component coupling of aldehydes, amines and trimethylsilyl cyanide using catalytic amount of zinc triflate at ambient temperature.
- Suresh,Chand, Subhash,Sandhu, Jagir S.
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p. 853 - 856
(2013/08/23)
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- MgI2 etherate-catalysed Strecker reaction: A facile and efficient synthesis of α-aminonitriles from aldimines and trimethylsilyl cyanide
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A mild and efficient procedure for the synthesis of a-aminonitriles is achieved by treatment of aldimines with trimethylsilyl cyanide catalysed by MgI2 etherate.
- Lu, Yongping,Wang, Yanping,Zhang, Xingxian
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p. 709 - 711
(2014/01/17)
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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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- Tin exchanged zeolite as catalyst for direct synthesis of α-amino nitriles under solvent-free conditions
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Sn exchanged HBeta zeolite was prepared and characterized by PXRD, surface area, TPD and TEM analysis. The Sn exchanged zeolite was found to be highly efficient catalyst for the direct synthesis of α-amino nitrile from various ketones and aldehydes with amine and trimethyl silylcyanide (TMSCN) under solvent-free condition. Excellent yield of α-amino nitrile (up to 96%) was achieved within 10-120 min at room temperature. The Sn exchanged HBeta zeolite was recovered and reused several times without the loss of its catalytic performance.
- Shah, Arpan K.,Khan, Noor-Ul H.,Sethia, Govind,Saravanan,Kureshy, Rukhsana I.,Abdi, Sayed H.R.,Bajaj, Hari C.
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experimental part
p. 22 - 30
(2012/06/29)
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