- New amine and aromatic substituted analogues of phencyclidine: Synthesis and determination of acute and chronic pain activities
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Background: Phencyclidine (PCP, I) is a synthetic drug with remarkable physiological properties. PCP and its analogues exert many pharmacological activities and interact with some neurotransmitter systems in the central nervous system like particular affinity for PCP sites in NMDA receptors or dopamine uptake blocking or even both. Aim and Objective: The following research, methyl group with electron-donating and dipole moment characters was added in different positions of phenyl ring along with the substitution of benzylamine (with many pharmacological effects) instead of piperidine ring of I to produce new compounds (II-V) of this family with more analgesic activities. Materials and Methods: Analgesic activities of these new compounds were measured by tail immersion and formalin tests for acute and chronic pains, respectively. Also, the outcomes were compared with control and PCP (10 mg/kg) groups. Results: The results indicate that compounds III, IV, and V have more acute and chronic antinociceptive effects than PCP and compound II which may be concerned with more antagonizing activities of these new painkillers for the blockage of dopamine reuptake as well as high affinity for NMDA receptors PCP binding site. Conclusion: It can be concluded that the benzylamine derivative of phencyclidine with a methyl group on the benzyl position on phenyl ring (V) is a more appropriate candidate to reduce acute and chronic (thermal and chemical) pains compared to other substituted phenyl analogs (II-IV) and PCP.
- Shokrollahi, Maryam,Samadizadeh, Marjaneh,Khalili, Mohsen,Sobhanian, Seyed A.,Ahmadi, Abbas
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p. 570 - 576
(2020/01/08)
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- Mechanochemical lignin-mediated strecker reaction
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A mechanochemical Strecker reaction involving a wide range of aldehydes (aromatic, heteroaromatic and aliphatic), amines, and KCN afforded a library of α-aminonitriles upon mechanical activation. This multicomponent process was efficiently activated by li
- Dabral, Saumya,Turberg, Mathias,Wanninger, Andrea,Bolm, Carsten,Hernández, José G.
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- Synthesis of novel magnetic nanoparticles with urea or urethane moieties: Applications as catalysts in the Strecker synthesis of α-aminonitriles
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Four novel magnetic nanoparticle catalysts with urea or urethane moieties are reported. The silica-coated magnetic nanoparticles were simply functionalized via addition of 3-(triethoxysilyl)propylisocyanate (TESPIC), amine or amino alcohol. TESPIC with dual labile functional groups was used as a suitable precursor for the synthesis of urethane-based catalysts. The newly synthesized catalysts were fully characterized using a variety of techniques. These functionalized magnetic nanoparticles were used as reusable catalysts in the Strecker synthesis of α-aminonitrile derivatives under solvent-free conditions at 50?°C.
- Baghery, Saeed,Zolfigol, Mohammad Ali,Schirhagl, Romana,Hasani, Masoumeh,Stuart, Marc C.A.,Nagl, Andreas
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- Mechanochemical Strecker Reaction: Access to α-Aminonitriles and Tetrahydroisoquinolines under Ball-Milling Conditions
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A mechanochemical version of the Strecker reaction for the synthesis of α-aminonitriles was developed. The milling of aldehydes, amines, and potassium cyanide in the presence of SiO2gave the corresponding α-aminonitriles in good to high yields. The high efficiency of the mechanochemical Strecker-type multicomponent reaction allowed the one-pot synthesis of tetrahydroisoquinolines after a subsequent internal N-alkylation reaction.
- Hernández, José G.,Turberg, Mathias,Schiffers, Ingo,Bolm, Carsten
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supporting information
p. 14513 - 14517
(2016/10/03)
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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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- Catalyst-free Strecker reaction in water: A simple and efficient protocol using acetone cyanohydrin as cyanide source
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A simple, convenient, and practical method for the synthesis of α-amino nitriles through a one-pot, three-component Strecker reaction of a carbonyl compound, amine, and acetone cyanohydrin in water has been developed. Reactions proceed very efficiently without any catalyst at room temperature with high chemoselectivity and give, in some cases, the expected α-amino nitrile pure after direct separation from water. The protocol is particularly efficient for both aliphatic and aromatic aldehydes, and cyclic ketones, in combination with primary and secondary amines. An unusual application of the Strecker reaction to 1,2-diamines to obtain 1,2-diamino nitriles, and to cyclic secondary amines is reported. Copyright
- Galletti, Paola,Pori, Matteo,Giacomini, Daria
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experimental part
p. 3896 - 3903
(2011/09/12)
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- Al-MCM-41 catalyzed three-component Strecker-type synthesis of α-aminonitriles
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Mesoporous aluminosilicate (Al-MCM-41) efficiently catalyzed the three-component Strecker-type reaction of benzylacetone and aniline with trimethylsilyl cyanide in CH2Cl2 at room temperature to afford the corresponding α-aminonitrile in excellent yields (up to 97%). Mesoporous silica (MCM-41), amorphous SiO2-Al2O3, and H-Y and H-ZSM-5 zeolites also catalyzed this reaction, but gave the desired product in lower yields. The Al-MCM-41 catalyzed three-component Strecker-type reaction was applicable to a wide range of ketones, aldehydes, and amines. Furthermore, the Al-MCM-41 catalyst could be applied to a fixed-bed flow reactor: The desired α-aminonitrile derivative was constantly produced in nearly 80% yields for 48 h.
- Iwanami, Katsuyuki,Seo, Hana,Choi, Jun-Chul,Sakakura, Toshiyasu,Yasuda, Hiroyuki
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experimental part
p. 1898 - 1901
(2010/04/06)
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- KSF-supported heteropoly acids catalyzed one-pot synthesis of α-aminonitriles
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In. the presence of KSF-supported heteropoly acid as a heterogeneous, reusable and inexpensive catalyst, three-component reactions between aldehydes or ketones, amines, and trimethylsilyl cyanide preceded to afford a-aminonitriles in excellent yields, very short reaction times, and low loading of catalyst. This catalyst was highly selective and other functional groups including carbon-carbon double bond, and heterocyclic moieties did not affect the reaction.
- Rafiee, Ezzat,Rashidzadeh, Solmaz,Eavani, Sara,Joshaghani, Mohammad
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experimental part
p. 209 - 215
(2011/11/29)
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- γ-Al2O3-supported 12-tungstosilicic acid as an efficient heterogeneous catalyst for the synthesis of α-aminonitrile
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The multicomponent Strecker reaction using trimethylsilyle cyanide was performed in very short reaction times, and α-aminonitriles were prepared in excellent yields in the presence of a catalytic amount of alumina-supported tungstosilicic acid. Copyright Taylor & Francis Group, LLC.
- Rafiee, Ezzat,Rashidzadeh, Solmaz,Joshaghani, Mohammad,Chalabeh, Hadi,Afza, Kambiz
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experimental part
p. 2741 - 2747
(2009/04/05)
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- K5CoW12O40·3H2O: Heterogeneous catalyst for the strecker-type aminative cyanation of aldehydes and ketones
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One-step synthesis of α-aminonitriles was successfully carried out by a three-component condensation of aldehydes or ketones, amines, and potassium cyanide in the presence of a catalytic amount of K5CoW12O40·3H2O as an efficient, reusable, and nontoxic catalyst. Copyright Taylor & Francis Group, LLC.
- Rafiee, Ezzat,Azad, Alireza
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p. 1127 - 1132
(2008/02/01)
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- [HP(HNCH2CH2)3N]NO3: An efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions
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In the presence of a catalytic amount of an azaphosphatrane nitrate salt, amines and thiols react readily with Michael acceptors. The salt is also an efficient promoter for the one pot synthesis of α-amino and α-amidonitriles. By anchoring the salt to Merrifield Resin, a reusable heterogeneous catalyst is obtained for these reactions. Evidence is presented for catalysis being attributable solely to the NO3- ion.
- Fetterly, Brandon M.,Jana, Nirmal K.,Verkade, John G.
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p. 440 - 456
(2007/10/03)
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- Iodine as a novel and efficient reagent for the synthesis of α-aminonitriles by a three-component condensation of carbonyl compounds, amines, and trimethylsilyl cyanide
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A straightforward and general method has been developed for the synthesis of α-aminonitriles by simply combining aldehydes or ketones, amines, and trimethylsilyl cyanides in the presence of a catalytic amount of molecular iodine at room temperature.
- Royer, Laurel,De, Surya K.,Gibbs, Richard A.
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p. 4595 - 4597
(2007/10/03)
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- Indium trichloride catalyzed one-step synthesis of α-amino nitriles by a three-component condensation of carbonyl compounds, amines and potassium cyanide
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A simple and general method has been developed for the synthesis of α-aminonitriles by a one-pot three-component condensation of aldehydes or ketones, amines and potassium cyanide in THF in presence of a catalytic amount of indium trichloride.
- Ranu, Brindaban C,Dey, Suvendu S,Hajra, Alakananda
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p. 2529 - 2532
(2007/10/03)
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