220130-50-7Relevant academic research and scientific papers
Mechanochemical Activation of Iron Cyano Complexes: A Prebiotic Impact Scenario for the Synthesis of α-Amino Acid Derivatives
Bolm, Carsten,Mocci, Rita,Schumacher, Christian,Turberg, Mathias,Puccetti, Francesco,Hernández, José G.
, p. 2423 - 2426 (2018)
Mechanochemical activation of iron cyano complexes by ball milling results in the formation of HCN, which can be trapped and incorporated into α-aminonitriles. This prebiotic impact scenario can be extended by mechanochemically transforming the resulting α-aminonitriles into α-amino amides using a chemical route related to early Earth conditions.
Magnetic Fe3O4-BF3: Highly efficient Lewis acid catalyst for the synthesis of α-aminonitriles
Shekouhy, Mohsen,Moaddeli, Ali,Khalafi-Nezhad, Ali
, p. 3805 - 3827 (2016/04/05)
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.
L-Proline catalyzed one pot synthesis of α-aminonitriles
Nasreen, Aayesha
, p. 3797 - 3800 (2013/07/05)
l-Proline (20 mol %) was found to be an efficient organocatalyst for one pot synthesis of a variety of α-aminonitriles from aldehydes, amines, and trimethylsilyl cyanide (TMSCN) in acetonitrile at ambient temperature giving good to excellent yields (72-95%).
Synthesis of α-aminonitriles using silica-bonded N-propylpiperazine sulfamic acid as a recyclable catalyst
Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
, p. 1103 - 1106,4 (2020/08/20)
α-Aminonitriles were synthesized via a one-pot three-component condensation of aldehydes, amines, and trimethylsilyl cyanide using silica-bonded N-propylpiperazine sulfamic acid (SBPPSA) as a recyclable solid acid at room temperature. SBPPSA showed much the same efficiency when used in consecutive reaction runs.
Silica-bonded N-propyl diethylenetriamine sulfamic acid as a recyclable solid acid catalyst for the synthesis of α-aminonitriles
Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
, p. 1095 - 1100 (2013/01/14)
Silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) is employed as a recyclable catalyst to synthesize a-aminonitriles. These syntheses involved one-pot condensation of an aldehyde, an amine, and trimethylsilyl cyanide under mild reaction conditions at room temperature. SBPDSA was recycled seven times in the condensation of benzaldehyde, aniline, and trimethylsilyl cyanide without reduction of its catalytic activity.
Silica-Bonded N-Propyl Diethylenetriamine Sulfamic Acid as a Recyclable Solid Acid Catalyst for the Synthesis of α-Aminonitriles
Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
, p. 1095 - 1100 (2015/06/30)
Silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) is employed as a recyclable catalyst to synthesize a-aminonitriles. These syntheses involved one-pot condensation of an aldehyde, an amine, and trimethylsilyl cyanide under mild reaction conditions at room temperature. SBPDSA was recycled seven times in the condensation of benzaldehyde, aniline, and trimethylsilyl cyanide without reduction of its catalytic activity.
Catalyst-free Strecker reaction in water: A simple and efficient protocol using acetone cyanohydrin as cyanide source
Galletti, Paola,Pori, Matteo,Giacomini, Daria
experimental part, p. 3896 - 3903 (2011/09/12)
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
Preparation of silica-based ionic liquid an efficient and recyclable catalyst for one-pot synthesis of α-aminonitriles
Nouri Sefat, Maryam,Saberi, Dariush,Niknam, Khodabakhsh
experimental part, p. 1713 - 1720 (2012/03/11)
Preparation of N-(3-silicapropyl) imidazolium hydrogen sulfate ([Sipim]HSO4) as a heterogeneous acidic ionic liquid is described. This heterogeneous ionic liquid was used as catalyst for the synthesis of α-aminonitriles by a one-pot condensation of aldehydes, amines, and trimethylsilyl cyanide at room temperature. Catalyst could be recycled for several times without any additional treatment. Graphical Abstract: A simple and efficient procedure for the preparation of silica-based acidic ionic liquid ([Sipim]HSO4) is described. This heterogeneous solid acid is employed as a catalyst for the synthesis of a-amino nitriles at room temperature. [Figure not available: see fulltext.]
Silica-bonded S-sulfonic acid: an efficient and recyclable solid acid catalyst for the three-component synthesis of α-amino nitriles
Niknam, Khodabakhsh,Saberi, Dariush,Sefat, Maryam Nouri
experimental part, p. 2959 - 2962 (2010/06/21)
Silica-bonded S-sulfonic acid (SBSSA) is employed as a recyclable catalyst for the synthesis of α-amino nitriles. These syntheses were performed via a one-pot three-component condensation of aldehydes, amines, and trimethylsilyl cyanide under mild reaction conditions at room temperature.
Water-mediated strecker reaction: An efficient and environmentally friendly approach for the synthesis of α-aminonitriles via a three-component condensation
Ramesh, Samikannu,Sivakumar, Kulanthaivel,Panja, Chiradeep,Arunachalam, Pirama Nayagam,Lalitha, Appaswami
experimental part, p. 3544 - 3551 (2011/01/12)
The synthesis of α-aminonitriles by a direct three component Strecker reaction has been achieved in water, which is found to be an inexpensive, non-toxic and eco-friendly reaction medium for the nucleophilic addition. This protocol is effective to a wide variety of substrates with different functional groups and does not require the use any other catalyst. Copyright Taylor & Francis Group, LLC.
