67490-38-4

Upstream product

• 60-29-7 diethyl ether 
• 74-90-8 hydrogen cyanide 
• 1077-18-5 N-benzylidenebutan-1-amine 
• 7677-24-9 trimethylsilyl cyanide 
• 100-52-7 benzaldehyde 
• 109-73-9 N-butylamine 
• 773837-37-9 sodium cyanide 
• 151-50-8 potassium cyanide 

Downstream Products

• 127749-49-9 2-Butylamino-2-phenyl-acetamide; hydrochloride 
• 1404295-96-0 methyl 2-({butyl[cyano(phenyl)methyl]amino}methyl)acrylate 

Relevant academic research and scientific papers

Catalyst-free multicomponent Strecker reaction in acetonitrile

The multicomponent Strecker reaction using trimethylsilyl cyanide was accomplished without any type of Lewis acid. The reaction performed in acetonitrile as solvent gave excellent results for any class of aldehydes (aromatic or aliphatic), as well as amines (aromatic or aliphatic). In many cases, α-aminonitrile product was isolated pure after the usual work-up, with quantitative chemical yields. A comparison between different solvents indicated that acetonitrile is the best choice. The rate comparison using different Lewis acids showed that all of them catalyzed the reaction in a similar extent, the difference with the acid Lewis-free being minimal.

Synthesis of α-Aminonitriles and 5-Substituted 1H-Tetrazoles Using an Efficient Nanocatalyst of Fe3O4@SiO2–APTES-supported Trifluoroacetic Acid

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.

Synthesis of novel magnetic nanoparticles with urea or urethane moieties: Applications as catalysts in the Strecker synthesis of α-aminonitriles

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.

Magnetic Fe3O4-BF3: Highly efficient Lewis acid catalyst for the synthesis of α-aminonitriles

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.

Zn(OAc)2·2H2O-catalyzed one-pot efficient synthesis of α-amino nitriles

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.

L-Proline catalyzed one pot synthesis of α-aminonitriles

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%).

A novel approach for the synthesis of α-aminonitriles using Mitsunobu's reagent under solvent-free conditions

A highly efficient, one-pot, three-component, solvent-free protocol for the synthesis of α-aminonitriles starting from their corresponding carbonyl compounds, amines, using Mitsunobu's reagent has been developed. Diversity of α-aminonitriles has been synthesized in good to excellent yields (80-99%) using various kinds of aldehydes/ketones and a variety of amines.

Sulfated tungstate: A green catalyst for Strecker reaction

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.

Sulfamic acid-functionalized magnetic Fe3O4 nanoparticles as an efficient and reusable catalyst for one-pot synthesis of α-amino nitriles in water

Grafting of chlorosulfuric acid on the amino-functionalized Fe 3O4 nanoparticles afforded sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (SA-MNPs) as a novel organic-inorganic hybrid heterogeneous catalyst, which was characterized by XRD, FT-IR, TGA, TEM, and elemental analysis. The catalytic activity of SA-MNPs was probed through one-pot synthesis of α-amino nitriles via three-component couplings of aldehydes (or ketones), amines and trimethylsilyl cyanide in water, at room temperature. The heterogeneous catalyst could be recovered easily and reused many times without significant loss of its catalytic activity.

Ga-TUD-1: A new heterogeneous mesoporous catalyst for the solventless expeditious synthesis of α-aminonitriles

The high surface area three-dimensional porous catalyst has been prepared and characterized by TEM, BET S.A, low angle XRD, 29Si MAS NMR, NH3 TPD techniques. A simple, efficient and rapid method for the green synthesis of α-aminonitriles has been demonstrated over a new mesoporous gallosilicate catalyst Ga-TUD-1. The solventless technique has been applied for the synthesis of a range of compounds with variable functionality with excellent yield and selectivity. The catalyst has been recycled four times with reproducible yield.