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Abstract
An efficient synthesis of functionalized spiropyrrolizidine oxindoles via a three-component tandem cycloaddition has been achieved. This strategy can provide direct and rapid access to spiropyrrolizidine oxindoles in high yields (up to 99%) with excellent diastereoselectivities (up to 99:1 dr). The features of this procedure are the following: mild reaction conditions, high yields, high diastereoselectivities, one-pot procedure and operational simplicity.
Highlights
Spirocyclic oxindoles are valuable synthetic intermediates and constitute the core units of many pharmacological agents and alkaloids [1,2,3]
Molecules 2011, 16 approach for the synthesis of five-membered heterocycles [34,35] and spiro-heterocycles, such as poly functionalized pyrrolidines [36,37,38,39], pyrazolidines and pyrrolizines [40,41], which widely occur in natural products and biologically active compounds
To the best of our knowledge, there are no reports concerning the synthesis of spiropyrrolizidine oxindoles 4 containing two ester groups or two amide groups, which could possess some interesting biological activities
Summary
Spirocyclic oxindoles are valuable synthetic intermediates and constitute the core units of many pharmacological agents and alkaloids [1,2,3]. These compounds have attracted much attention from synthetic chemists due to their diverse biological activities including antimycobacterial [4,5,6,7,8,9], antitumor [10,11,12,13,14], antimicrobial [15], antibacterial [16,17], antifungal [18,19], antiviral [20,21], and local anesthetic [22] properties. We report a three-component tandem cycloaddition reaction between substituted isatins, L-proline and maleates (maleamide) that produces such structures
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