Abstract
2-Aminopyridine, unlike the 3- and 4-isomers, is animated by sodium amide with the formation of 2,6-diaminopyridine. Among the dimethylaminopyridines, the 3- and 4-isomers are more active in the Chichibabin reaction, while 2-dimethylaminopyridine is converted with great difficulty under the action of sodium amide into 2,6-diaminopyridine with the initial replacement of the dimethylamine residue by an amino group. Azaindoles and azaindolines do not take part in the animation reaction. In 1-phenyl-5-azaindole, under the action of sodium amide, the pyrrole ring opens with the formation of 4-anilino-3-vinylpyridine.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1232–1239, September, 1973.
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Pozharskii, A.F., Kuz'menko, V.V., Azimov, V.A. et al. The Chichibabin reaction in the Aminopyridine, azaindole, and azaindoline series. Chem Heterocycl Compd 9, 1119–1125 (1973). https://doi.org/10.1007/BF00474785
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DOI: https://doi.org/10.1007/BF00474785