Chichibabin pyridine synthesis

Not to be confused with Chichibabin reaction.

Chichibabin pyridine synthesis
Named after Aleksei Chichibabin
Reaction type Ring forming reaction
Identifiers
RSC ontology ID RXNO:0000526

The Chichibabin pyridine synthesis (/ˈtʃiːtʃiːˌbeɪbiːn/) is a method for synthesizing pyridine rings. The reaction involves the condensation reaction of aldehydes, ketones, α,β-Unsaturated carbonyl compounds, or any combination of the above, with ammonia.[1] It was reported by Aleksei Chichibabin in 1924.[2][3] Methyl-substituted pyridines, which show widespread uses among multiple fields of applied chemistry, are prepared by this methodology.[4]

  1. ^ Frank, R. L.; Seven, R. P. (1949). "Pyridines. IV. A Study of the Chichibabin Synthesis". Journal of the American Chemical Society. 71 (8): 2629–35. doi:10.1021/ja01176a008.
  2. ^ Tschitschibabin, A. E. (1924). "Über Kondensation der Aldehyde mit Ammoniak zu Pyridinbasen". Journal für Praktische Chemie. 107 (1–4): 122–8. doi:10.1002/prac.19241070110.
  3. ^ Li, J. J. (2009). "Chichibabin pyridine synthesis". Name Reactions. pp. 107–9. doi:10.1007/978-3-642-01053-8_51. ISBN 978-3-540-40203-9.
  4. ^ Sagitullin, R. S.; Shkil, G. P.; Nosonova, I. I.; Ferber, A. A. (1996). "Synthesis of pyridine bases by the Chichibabin method (review)". Chemistry of Heterocyclic Compounds. 32 (2): 127–40. doi:10.1007/BF01165434. S2CID 93717043.