The Cs2CO3-Catalyzed Reaction of 2-Oxindoles with Enones for the Preparation of Indolin-3-Ones and Their Further Transformation

Ying Shao; Yu-Mei Zeng; Jie-Ying Ji; Xiao-Qiang Sun; Hai-Tao Yang; Chun-Bao Miao

doi:10.1021/acs.joc.6b01993

The Cs₂CO₃-Catalyzed Reaction of 2-Oxindoles with Enones for the Preparation of Indolin-3-Ones and Their Further Transformation

J Org Chem. 2016 Dec 16;81(24):12443-12450. doi: 10.1021/acs.joc.6b01993. Epub 2016 Nov 29.

Authors

Ying Shao¹, Yu-Mei Zeng¹, Jie-Ying Ji¹, Xiao-Qiang Sun¹, Hai-Tao Yang¹, Chun-Bao Miao¹

Affiliation

¹ Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, School of Petrochemical Engineering, Changzhou University , Changzhou 213164, China.

PMID: 27978718
DOI: 10.1021/acs.joc.6b01993

Abstract

The Cs₂CO₃-catalyzed reaction of 2-oxindoles with enones affords 2,2-disubstituted indolin-3-ones through domino "Michael addition-oxidation-ring-cleavage-C-N coupling" process. O₂ acts as the sole oxidant to accomplish the oxidative process. The indolin-3-ones can be further transformed to pyridazine, azirdine-fused 3-oxindoles, 4-quinolone derivatives easily.

Publication types

Research Support, Non-U.S. Gov't