A. P. Krinochkin, M. R. Guda, A. Rammohan, D. S. Kopchuk, I. L. Nikonov, E. D. Ladin, S. Santra, I. N. Egorov, G. V. Zyryanov, O. N. Chupakhin, “Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the $\mathrm{S_N^{ipso}}$/aza-Diels–Alder reaction sequence”, Mendeleev Commun., 2022, Volume 32, Issue 6,Pages 726

This article is cited in 3 papers

Communications

Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the $\mathrm{S_N^{ipso}}$/aza-Diels–Alder reaction sequence

A. P. Krinochkin^ab, M. R. Guda^b, A. Rammohan^b, D. S. Kopchuk^ab, I. L. Nikonov^ab, E. D. Ladin^b, S. Santra^b, I. N. Egorov^b, G. V. Zyryanov^ab, O. N. Chupakhin^b

^a I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^b Institute of Chemical Engineering, Ural Federal University, Ekaterinburg, Russian Federation

Abstract: Reaction between 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines with the following aza-Diels–Alder autoclave reaction affords hardly available 2-amino-3,6-di(het)aryl-pyridines in up to 67% yield after two steps and in 75% yield for the one-pot way. The compounds obtained can be promising for medicinal chemistry.

Keywords: 2-aminopyridines, 6-amino-2,2'-bipyridines, 1,2,4-triazines, arylhydrazines, ipso-substitution, aza-Diels-Alder reaction, autoclave processes.

Language: English

DOI: 10.1016/j.mencom.2022.11.006

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