Chichibabin reaction

The synthesis is reminiscent of the Chichibabin reaction.

They include the Chichibabin reaction which yields pyridine derivatives aminated at the 2-position.

It is produced by the reaction of sodium amide with pyridine, the Chichibabin reaction.

The other reactions are the Bodroux-Chichibabin aldehyde synthesis and the Chichibabin reaction.

The Chichibabin reaction is a nucleophilic substitution on the pyridine ring; the 2nd and 6th positions are therefore favoured over the other positions.

One classic reaction is the Chichibabin reaction (Aleksei Chichibabin, 1914) in which pyridine is reacted with an alkali-metal amide such as sodium amide to form 2-aminopyridine.

Before the Chichibabin reaction, only electrophilic substitution on the pyridine ring was possible, which is difficult because pyridine is an electron-poor aromatic compound and additionally forms positive charged pyridinum ions, which further decrease the probability of an electrophile attack.