86926-55-8

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 10283-95-1 N-allylbenzamide 
• 68003-55-4 benzylidene allylamine 
• 74-90-8 hydrogen cyanide 
• 68003-55-4 (E)-N-allylbenzylideneimine 
• 100-52-7 benzaldehyde 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 107-11-9 1-amino-2-propene 

Downstream Products

• 1008-89-5 2-phenylpyridine 
• 91180-54-0 2-(N-allylamino)-2-phenylacetamide 

Relevant academic research and scientific papers

Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

An iridium-catalyzed reductive nucleophilic addition to secondary amides is reported. After the iridium-catalyzed reduction, the resulting imines can undergo the Strecker reaction, the Mannich reaction, allylation, and [3 + 2]-cycloaddition. The method sh

Carbohydrates as efficient catalysts for the hydration of α-amino nitriles

Directed hydration of α-amino nitriles was achieved under mild conditions using simple carbohydrates as catalysts exploiting temporary intramolecularity. A broadly applicable procedure using both formaldehyde and NaOH as catalysts efficiently hydrated a variety of primary and secondary susbtrates, and allowed the hydration of enantiopure substrates to proceed without racemization. This work also provides a rare comparison of the catalytic activity of carbohydrates, and shows that the simple aldehydes at the basis of chemical evolution are efficient organocatalysts mimicking the function of hydratase enzymes. Optimal catalytic efficiency was observed with destabilized aldehydes, and with difficult substrates only simple carbohydrates such as formaldehyde and glycolaldehyde proved reliable.

A short synthesis of pyridines from deprotonated α-aminonitriles by an alkylation/RCM sequence

α-Aminonitriles can serve as versatile key precursors for the synthesis of nitrogen containing heterocycles. After unsuccessful trials involving the [1,2]-Stevens rearrangement of nitrile-stabilized ammonium ylides, we herein report a simple three-step synthesis of substituted pyridines based on an alkylation/ring-closing metathesis/aromatization sequence.

Solvent-free synthesis of racemic α-aminonitriles

A very simple one-step, environmentally friendly procedure for the synthesis of α-aminonitriles from aldehydes and ketones, using trimethylsilyl cyanide in the absence of solvent, is reported. The active catalyst of this three-component (Strecker) reaction was the amine employed in the transformation. In general, aldehydes react more rapidly than ketones and give almost quantitative yields of the corresponding α-aminonitriles in less than fifteen minutes. However, only cyclic ketones afford the corresponding α-aminonitriles in excellent chemical yields under these conditions. Georg Thieme Verlag Stuttgart.

The Strecker reaction: Kinetic and equilibrium studies of cyanide addition to iminium ions

Kinetics studies are reported of the reactions of benzylidene benzylamine, 4a, and of benzylidene allylamine, 4b, with cyanide in aqueous buffers to give the corresponding a-aminonitriles. The results allow the calculation of values of rate and equilibrium constants for reaction of the iminium ions formed from 4a and 4b with cyanide ions. These values are compared with those, obtained from the hydrolysis reactions, for reaction of the iminium ions with hydroxide ions and with water. Comparison with some other iminium ions reveals that those formed from 4a and 4b are relatively unreactive due to the possibilities of charge delocalisation.

Trimethylsilyl cyanide addition to aldimines and its application in the synthesis of (S)-phenylglycine methyl ester

The addition of TMSCN to a variety of arylaldimines (Strecker reaction) in the presence of LiClO4 or BF3?Et2O in acetonitrile has been studied. The reaction provided the addition products in very high yields. The method has been successfully utilized for the synthesis of (S)-phenylglycine methyl ester.