M. I. Savchuk, I. S. Kovalev, V. L. Rusinov, D. S. Kopchuk, A. P. Krinochkin, G. V. Zyryanov, O. N. Chupakhin, V. N. Charushin, “Rapid metal free construction of 3-positioned 2-pyridyl substituent in indoles”, Mendeleev Commun., 2020, Volume 30, Issue 6,Pages <nobr>712

This article is cited in 7 papers

Communications

Rapid metal free construction of 3-positioned 2-pyridyl substituent in indoles

M. I. Savchuk^a, I. S. Kovalev^a, V. L. Rusinov^ab, D. S. Kopchuk^ab, A. P. Krinochkin^ab, G. V. Zyryanov^ab, O. N. Chupakhin^ab, V. N. Charushin^ab

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

Abstract: New access to substituted 2-(indol-3-yl)pyridines involves two stage protocol, namely, a reaction of deoxygenative nucleophilic substitution of hydrogen in 1,2,4-triazine-4-oxides under the action of indoles followed by aza-Diels–Alder reaction of thus obtained 5-indolyl-1,2,4-triazines with 2,5-norbornadiene in a pressure vessel. The reactions sequence provides good yields and is suitable for wide scope of substituted 1,2,4-triazines.

Keywords: 2-(indol-3-yl)pyridines, nucleophilic substitution of hydrogen, aza-Diels–Alder reaction, 1,2,4-triazines, pyridines.

Language: English

DOI: 10.1016/j.mencom.2020.11.007

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