Chichibabin reaction
The Chichibabin reaction (pronounced ' (chē')-chē-bā-bēn) is a method for producing 2-aminopyridine derivatives by the reaction of pyridine with sodium amide. It was reported by Aleksei Chichibabin in 1914. The following is the overall form of the general reaction:
| Chichibabin reaction | |
|---|---|
| Named after | Aleksei Chichibabin |
| Reaction type | Substitution reaction |
| Identifiers | |
| RSC ontology ID | RXNO:0000527 |
The direct amination of pyridine with sodium amide takes place in liquid ammonia. Following the addition elimination mechanism first a nucleophilic NH2− is added while a hydride (H−) is leaving.
Ciganek describes an example of an intramolecular Chichibabin reaction in which a nitrile group on a fused ring is the source of nitrogen in amination.
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