Synthesis of Some Nitropyridylacetonitriles

Facile Synthesis of Aryl-Pyridyl, Pyridazinyl, Pyrazinyl, and Triazinyl Acetonitriles

“…It has been reported that tert ‐butyl cyanoacetate undergoes nucleophilic displacement of nitro‐activated 2‐chloropyridines using boiling tetrahydrofuran in the presence of potassium carbonate as base to yield the corresponding tert ‐butyl cyanoacetate pyridine, which can be dealkoxycarbonylated in the presence of p ‐toluene sulfonic acid in boiling toluene to give the acetonitriles analogues . This methodology has also been applied to monochloro pyrimidines .…”

Mild Addition of Nucleophiles to Pyridine-N-Oxides

“…One method for their preparation is the direct displacement of the corresponding 2-halopyridines with nucleophiles (Scheme ). Although amines are the most frequent reaction partner, there are many examples with alkoxy, thiol, and alkyl nucleophiles. Yields for these transformations, particularly on unactivated 2-halopyridines, are commonly low and in most cases require metal catalysis and/or high temperature and pressure.…”

α-Heteroarylation of Esters, Lactones, Amides, and Lactams by Nucleophilic Aromatic Substitution

“…Alternatively, nucleophilic aromatic substitution (S N Ar) (Scheme ) may present advantages. Previous reports of such transformations involving ester enolates are limited to doubly stabilized enolates such as malonates, malonitriles, , ammonium ylide esters, and α-iminoesters . Herein, we report a mild and general protocol to prepare α-heteroaryl esters or amides using readily available heterocyclic chlorides and simple ester or amide enolates.…”