Issue 16, 2019
From the journal:

Organic & Biomolecular Chemistry

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

Piyush Tehria  and  Rama Krishna Peddinti ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology, Roorkee-247667, Uttarakhand, India
E-mail: rkpedfcy@iitr.ac.in, ramakpeddinti@gmail.com

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

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Article information

DOI
https://doi.org/10.1039/C9OB00385A
Article type
Paper
Submitted
16 Feb 2019
Accepted
27 Mar 2019
First published
03 Apr 2019

Org. Biomol. Chem., 2019,17, 3964-3970

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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

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