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RESEARCH ARTICLE
Contents Vol 67(5)

DABCO Promoted Regioselective Synthesis of New Diversely Functionalized 3-Hydroxy-2-Oxindole Scaffolds

Pramod B. Thakur A , Jagdeesh B. Nanubolu B and Harshadas M. Meshram A C
+ Author Affiliations
- Author Affiliations

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

B Laboratory of X-Ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.

C Corresponding author. Email: hmmeshram@yahoo.com

Australian Journal of Chemistry 67(5) 768-776 https://doi.org/10.1071/CH13580
Submitted: 27 October 2013  Accepted: 19 December 2013   Published: 31 January 2014

Abstract

An efficient and highly regioselective γ-addition of β-keto sulfones on isatins has been achieved in the presence of a catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO) to afford a γ-(3-hydroxy-2-oxindole)-β-keto sulfone structural framework. The scope of the method is tested by screening a series of isatin electrophiles as well as β-keto sulfones. The described method was found to be very handy and provides straightforward access for the diversely functionalized 3-β-keto sulfone substituted-3-hydroxy-2-oxindole structural scaffolds in very good yields from readily available starting materials under metal-free reaction conditions.


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