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RESEARCH ARTICLE
Contents Vol 68(3)

An Exploration of Organocatalyst 1,4-Diazabicyclo[2.2.2]octane in the Direct Regioselective and Chemoselective γ-Addition of β-Keto Amide on Isatin to Afford Structurally Diverse Molecular Frameworks

Pramod B. Thakur A and Harshadas M. Meshram A B
+ Author Affiliations
- Author Affiliations

A Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.

B Corresponding author. Email: hmmeshram@yahoo.com

Australian Journal of Chemistry 68(3) 453-460 https://doi.org/10.1071/CH14239
Submitted: 13 April 2014  Accepted: 11 June 2014   Published: 29 September 2014

Abstract

An efficient protocol promoted by 1,4‐diazabicyclo[2.2.2]octane is described for the regioselective and chemoselective γ-addition of β-keto amides on isatins to afford γ-(3-hydroxy-2-oxindole)-β-keto amide structural framework under metal-free conditions. The developed method is mild, generates high yields, and is applicable for a variety of isatin electrophiles as well as β-keto amides. Moreover, the procedure is very handy and environmentally benign in nature, and provides direct access for the synthesis of diverse functionalized 3-β-keto amide-substituted 3-hydroxy-2-oxindole structural scaffolds from readily available starting materials.


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