Jump to main content
Jump to site search

Issue 16, 2019
Previous Article Next Article

DBU-catalyzed [3 + 2] cycloaddition and Michael addition reactions of 3-benzylidene succinimides with 3-ylidene oxindoles and chalcones

Author affiliations

Abstract

A metal-free DBU catalyzed protocol has been developed for the regioselective [3 + 2] cycloaddition reactions of 3-benzylidene succinimides with 3-ylidene oxindoles to furnish spirooxindole derivatives. The 3-benzylidene succinimides underwent Michael addition with chalcones to provide benzylidene succinimide-tethered propanones. All the reactions proceeded under mild conditions and the products were isolated by simple filtration and washing with ethanol in good yields. The current methodology utilizes simple precursors and provides functionally-rich succinimides with two to five contiguous stereocenters in excellent diastereoselectivity and with complete regioselectivity.

Graphical abstract: DBU-catalyzed [3 + 2] cycloaddition and Michael addition reactions of 3-benzylidene succinimides with 3-ylidene oxindoles and chalcones

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Feb 2019, accepted on 27 Mar 2019 and first published on 03 Apr 2019


Article type: Paper
DOI: 10.1039/C9OB00385A
Citation: Org. Biomol. Chem., 2019,17, 3964-3970

  •   Request permissions

    DBU-catalyzed [3 + 2] cycloaddition and Michael addition reactions of 3-benzylidene succinimides with 3-ylidene oxindoles and chalcones

    P. Tehri and R. K. Peddinti, Org. Biomol. Chem., 2019, 17, 3964
    DOI: 10.1039/C9OB00385A

Search articles by author

Spotlight

Advertisements