Issue 99, 2015

A novel one-pot multi-component synthesis of 3,3’-disubstituted oxindole and spirooxindole scaffolds via Sn-catalyzed C(sp3)–H functionalization of azaarenes by sequential Knoevenagel–Michael-cyclization reaction

Abstract

Sn-catalyzed C(sp3)–H bond functionalization of 2-methyl azaarenes/2-(azaaryl)methanes has been achieved for the first time in a one-pot multi-component reaction with isatin and active methylene compounds via tandem sequential Knoevenagel–Michael-intramolecular C–N cyclization. This strategy provides new cost-effective access to potent and biologically/medicinally important spirooxindoles/3,3′-disubstituted 2-oxindoles in good to excellent yields.

Graphical abstract: A novel one-pot multi-component synthesis of 3,3’-disubstituted oxindole and spirooxindole scaffolds via Sn-catalyzed C(sp3)–H functionalization of azaarenes by sequential Knoevenagel–Michael-cyclization reaction

Supplementary files

Article information

Article type
Communication
Submitted
13 Aug 2015
Accepted
07 Sep 2015
First published
07 Sep 2015

RSC Adv., 2015,5, 81103-81107

Author version available

A novel one-pot multi-component synthesis of 3,3’-disubstituted oxindole and spirooxindole scaffolds via Sn-catalyzed C(sp3)–H functionalization of azaarenes by sequential Knoevenagel–Michael-cyclization reaction

S. S. Chavan, M. Y. Pathan, S. H. Thorat, R. Gonnade and S. A. R. Mulla, RSC Adv., 2015, 5, 81103 DOI: 10.1039/C5RA16334J

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