Jump to main content
Jump to site search


A regio- and stereocontrolled approach to the synthesis of 4-CF3-substituted spiro[chromeno[3,4-c]pyrrolidine-oxindoles] via reversible [3+2] cycloaddition of azomethine ylides generated from isatins and sarcosine to 3-nitro-2-(trifluoromethyl)-2H-chromenes

Author affiliations

Abstract

A one-pot three-component reaction of azomethine ylides generated in situ from isatins and sarcosine with 3-nitro-2-(trifluoromethyl)-2H-chromenes in i-PrOH at 55–60 °C leads to the kinetically controlled products – exo-spiro[chromeno[3,4-c]pyrrolidine-3,3′-oxindoles]. When this reaction is carried out in 1,4-dioxane under reflux, the thermodynamically controlled endo-spiro[chromeno[3,4-c]pyrrolidine-1,3′-oxindoles] are preferably formed. The isomerization of the kinetic products in DMSO solution at different temperatures has been studied by NMR spectroscopy and the stepwise mechanism of reversible [3+2] cycloaddition has been confirmed. The cytotoxic activity of some CF3-substituted spiro[chromeno[3,4-c]pyrrolidine-oxindoles] against the HeLa cell line was evaluated by the MTT test.

Graphical abstract: A regio- and stereocontrolled approach to the synthesis of 4-CF3-substituted spiro[chromeno[3,4-c]pyrrolidine-oxindoles] via reversible [3+2] cycloaddition of azomethine ylides generated from isatins and sarcosine to 3-nitro-2-(trifluoromethyl)-2H-chromenes

Back to tab navigation

Supplementary files

Publication details

The article was received on 31 Aug 2019, accepted on 26 Oct 2019 and first published on 28 Oct 2019


Article type: Paper
DOI: 10.1039/C9NJ04498A
New J. Chem., 2019, Advance Article

  •   Request permissions

    A regio- and stereocontrolled approach to the synthesis of 4-CF3-substituted spiro[chromeno[3,4-c]pyrrolidine-oxindoles] via reversible [3+2] cycloaddition of azomethine ylides generated from isatins and sarcosine to 3-nitro-2-(trifluoromethyl)-2H-chromenes

    I. B. Kutyashev, M. V. Ulitko, A. Yu. Barkov, N. S. Zimnitskiy, V. Yu. Korotaev and V. Ya. Sosnovskikh, New J. Chem., 2019, Advance Article , DOI: 10.1039/C9NJ04498A

Search articles by author

Spotlight

Advertisements