In previous papers from this laboratory (1, 2) it has been reported that a-amino acids undergo a quantitative decarboxylation.in aqueous solution when treated with N-bromosuccinimide. Under the conditions used\ (a temperature of 30” and a pH of 3 to 5), the reaction was complete in 30 minutes. Anomalies in behavior were observed with glycine and /3-alanine. The consumption of N-bromosuccinimide...

Palladium-catalyzed decarboxylative alpha-allylation of nitriles readily occurs with use of Pd(2)(dba)(3) and rac-BINAP. This catalyst mixture also allows the highly regiospecific alpha-allylation of nitriles in the presence of much more acidic alpha-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, m...

Sulfur-containing nitriles have important research value in the life sciences due to their diverse biological activities resulting from the sulfur and cyano functional groups. Herein, a copper-catalyzed cyanothiolation of N-tosylhydrazones with thiocyanates to generate a-arylthioalkanenitriles bearing sulfur-substituted quaternary carbon center atoms has been described. This novel protocol invo...

The importance of nitriles as a key class chemicals with applications across the sciences is widely appreciated. natural world an underappreciated source chemically diverse nitriles. With this in mind, review describes novel nitrile-containing molecules isolated from sources 1998 to 2021, well discussion biological activity these compounds. This study gathers 192 varied origins plant, animal, a...

The first example of copper-catalyzed ring-opening, enantioselective arylation cyclic ketoxime esters to access ω,ω-diaryl alkyl nitriles has been developed in high yield (up 92% yield) with excellent enantioselectivity 91% ee). Side-arm bis(oxazoline) ligand plays a significant role this asymmetric catalytic transformation, which provides an efficient route construct diverse chiral nitriles. S...

2-Amino-4-benzoyl-1-arylpyrrole-3-carbonitriles react with arylidene malonodinitriles, β-ketoesters and βdiketones to afford pyrrolo[2,3-b]pyridine derivatives.

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...

Nickel(0) catalysts were used to produce substituted imidazoles in good to high yields using benzonitrile, p-substituted benzonitriles and 4-cyanopyridine as starting materials.

Hydrogenation of nitriles to primary amines with heterogeneous catalysts under liquid-phase continuous-flow conditions is described. Newly developed polysilane/SiO2-supported Pd was found to be an effective catalyst and various nitriles were converted into primary amine salts in almost quantitative yields under mild reaction conditions. Interestingly, a complex mixture was obtained under batch ...