Reação de Chichibabin

A reação de Chichibabin (pronuncia-se tchi-tchi-bá-bin) é um metodo de produção de derivados de 2-aminopiridina pela reação da piridina com amida de sódio. Foi relatada por Aleksei Chichibabin em 1914. O seguinte é a fórmula geral da reação:
Reação de Chichibabin

A aminação direta da piridina com amida de sódio ocorre em amônia líquida. Segundo o mecanismo de adição-eliminação, um nucleófilo NH2- é adicionado enquanto um hidreto (H-) é eliminado.

Antes de Chichibabin, somente a substituição eletrofílica no anel piridínico era possível, o que é difícil devido ao fato de a piridina ser um composto aromático pobre em elétrons e formar íons positivos piridínio, reduzindo posteriormente a possibilidade de um ataque eletrófilo. As posições atacadas pelo eletrófilo na piridina são a 3 e a 5.

A reação de Chichibabin é uma substituição nucleofílica no anel da piridina; as posições 2 e 6 são favorecidas em relação às outras.

Mecanismo de reação

Reação geral de Chichibabin

Ver também

Referências

  • A. E. Chichibabin and O. A. Zeide (1914). «.». Zhur. Russ. Fiz. Khim. Obshch (J. Russ. Phys. Chem. Soc.). 46. 1212 páginas 
  • A F Pozharskii, A M Simonov, V N Doron'kin (1978). «Advances in the Study of the Chichibabin Reaction». Russian Chemical Reviews. 47 (11): 1042–1060. Bibcode:1978RuCRv..47.1042P. doi:10.1070/RC1978v047n11ABEH002292 
  • R. Norris Shreve, E. H. Riechers, Harry Rubenkoenig, and A. H. Goodman (1940). «Amination in the Heterocyclic Series By Sodium Amide». Industrial & Engineering Chemistry. 32 (2): 173–178. doi:10.1021/ie50362a008 
  • FW Bergstrom, HG Sturz, HW Tracy (1946). «The Use of the Fused Eutectic of Sodium amide and Potassium amide in Organic Synthesis». The Journal of Organic Chemistry. 11 (3): 239–246. PMID 20983300. doi:10.1021/jo01173a005 

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