BACKGROUND The classical Strecker reaction is one of the simplest and most economical methods for the synthesis of racemic α-aminonitriles (precursor of α-amino acids) and pharmacologically useful compounds. RESULTS Indium powder in water is shown to act as a very efficient catalyst for one-pot, three-component synthesis of α-aminonitriles from diverse amines, aldehydes and TMSCN. This genera...

The preparation of O-methylimidates from alpha-aminonitriles and their subsequent co-cyclization with primary amines to afford 4-substituted 5-aminoimidazoles was studied. It was found that the mildly acidic pyridinium p-toluenesulfonate efficiently catalyzed each stage of the reaction sequence: (a) the formation of the O-methylimidates, (b) their co-cyclization with a variety of primary amines...

Ruthenium-catalyzed oxidative cyanation of tertiary amines with molecular oxygen in the presence of sodium cyanide and acetic acid gives the corresponding alpha-aminonitriles, which are highly useful intermediates for organic synthesis. The reaction is the first demonstration of direct sp(3) C-H bond activation alpha to nitrogen followed by carbon-carbon bond formation under aerobic oxidation c...

addition of potassium cyanide to a mixture of schiff base and lithium perchlorate afforded a-aminonitriles in high yields. addition of potassium cyanide to a methanolic solution of schiff base and phosphoric acid afforded a-aminonitriles. when the reaction mixture was refluxed it gave a-amino acids in high yields.

The reaction of arylidenemalonodinitriles 1 with 1-arylethylidenemalonodinitriles 2 gives rise to sub­ stituted cyclohexadiene derivatives 3 which then undergo elimination of hydrogen cyanide and afford 3,5-diaryl-2,6-dicyano-aminobenzenes 4. This reac­ tion is a modification of more general dimerization reaction involving ylidenemalonodinitriles synthe­ sized from a variety of ketones. These t...

Two representative members of the phenanthropiperidine alkaloid family, tylophorine (1) and cryptopleurine (2), were synthesized by a bidirectional alkylation strategy employing dibenzylaminoacetonitrile as substrate. This approach relies on unprecedented condensation metallated α-aminonitriles with bromomethylphenanthrenes to provide fully substituted α-aminonitriles, which are subjected NaBH4...

The functional group transformation associated with nitrile moiety is considered a diligent research topic in the synthetic community as it building block for several organic molecules, including ketones and amides. Many methodologies have been developed synthesizing amides, considering them analogues exciting biological properties. However, there are limited articles to synthesize these import...

A general method for the one-pot, three-component Strecker reaction of ketones was developed using Brønsted acids as organocatalysts. A series of alpha-aminonitriles were obtained in good to excellent yields (79-99%). A preliminary extension to a catalytic enantioselective three-component Strecker reaction of ketones (up to 40% ee) is also described.

Owing to their various modes of reactivity, aaminonitriles represent versatile building blocks for the construction of a wide range of nitrogen heterocycles. The present Concept article focuses on synthetic methodologies using their bifunctional nature which is the basis of their reactivity as a-amino carbanions and as iminium ions. Reactions exclusively taking place on either the amine or on t...

Oxidative α-cyanation of tertiary amines is catalyzed by gold complexes with trimethylsilyl cyanide to afford the corresponding α-aminonitriles in the presence of tert-butyl hydroperoxide in good to excellent yields under acid-free conditions at room temperature.