Chichibabin Reaction

A. E. Chichibabin, O. A. Zeide, J. Russ. Phys. Chem. Soc. 46, 1216 (1914), C.A. 9, 1901 (1915).

Amination of s and other heterocyclic nitrogen compounds with alkali-metal amides:



H. S. Mosher, Heterocyclic Compounds 1, 405 (1950); A. F. Pozharskii et al., Russ. Chem. Rev. 47, 1042 (1978); H. J. W. van den Haak et al., J. Org. Chem. 46, 2134 (1981). Applications: N. J. Kos et al., ibid. 44, 3140 (1979); H. Tondys et al., J. Heterocyclic Chem. 22, 353 (1985); E. Ciganek et al., J. Org. Chem. 57, 4521 (1992). Review: H. C. van der Plas, M. Wozniak, Croat. Chem. Acta 59, 33-49 (1986). Cf. Kröhnke Pyridine Synthesis.