Not to be confused with Chichibabin pyridine synthesis.
Chichibabin reaction
Named after
Aleksei Chichibabin
Reaction type
Substitution reaction
Identifiers
RSC ontology ID
RXNO:0000527
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.[1] The following is the overall form of the general reaction:
Chichibabin overall reaction
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.[2]
^Chichibabin, A. E.; Zeide, O. A. (1914). "New Reaction for Compounds Containing the Pyridine Nucleus". Zhur. Russ. Fiz. Khim. Obshch (J. Russ. Phys. Chem. Soc.). 46: 1216–36.
^Ciganek, E. (1992). "Tertiary Carbinamines by Addition of Organocerium Reagents to Nitriles and Ketimines". Journal of Organic Chemistry. 57 (16): 4521–7. doi:10.1021/jo00042a037.
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1126/SCIENCE.198.4314.251. PMID 17770484. Korey, William (1980). "American reaction to the Shcharansky case". American Jewish Year Book. 80: 118–129. JSTOR 23603826...
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