Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines

The sequential three-component reaction between o-hydroxybenzaldehydes, N-(cyanomethyl)pyridinium salts and a nucleophile towards substituted chromenoimidazopyridines under oxidative conditions has been developed. The employment of Mn(OAc)3•2H2O or KMnO4 as stoichiometric oxidants allowed the use of a wide range of nucleophiles, such as nitromethane, (aza)indoles, pyrroles, phenols, pyrazole, indazole and diethyl malonate. The formation of the target compounds presumably proceeds through a domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction sequence. © 2018 Storozhenko et al.; licensee Beilstein-Institut. License and terms: see end of document.

Publisher
Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
Language
English
Pages
3078-3087
Status
Published
Volume
14
Year
2018
Organizations
  • 1 Organic Chemistry Department, Peoples' Friendship University of Russia, RUDN University, Miklukho-Maklaya st. 6, Moscow, 117198, Russian Federation
  • 2 Department of Chemistry, North Caucasus Federal University, Pushkin st. 1a, Stavropol, 355009, Russian Federation
Keywords
2-aminochromene; 2-iminochromene; Domino reaction; Imidazo[1,2-a]pyridine; Michael addition; Multicomponent reaction; Oxidation; Pyridine amination
Date of creation
04.02.2019
Date of change
04.02.2019
Short link
https://repository.rudn.ru/en/records/article/record/36417/
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