Issue 125, 2015

Highly diastereoselective synthesis of imidazolidine-dispirooxindoles via three-component [3 + 2] cycloadditions of isatins, 2-(aminomethyl)pyridine and isatin-based imines

Abstract

In the presence of Et3N, the [3 + 2] cycloaddition of isatins, 2-(aminomethyl)pyridine and isatin-based imines proceeded readily, and furnished novel imidazolidine-dispirooxindoles in up to 84% yield with up to >99 : 1 diastereoselectivity. The relative configuration of the imidazolidine-dispirooxindoles was firmly confirmed on the basis of X-ray single crystal structure analysis. The reaction mechanism was assumed to account for the diastereoselective formation of the imidazolidine-dispirooxindoles.

Graphical abstract: Highly diastereoselective synthesis of imidazolidine-dispirooxindoles via three-component [3 + 2] cycloadditions of isatins, 2-(aminomethyl)pyridine and isatin-based imines

Supplementary files

Article information

Article type
Paper
Submitted
21 Oct 2015
Accepted
24 Nov 2015
First published
26 Nov 2015

RSC Adv., 2015,5, 103116-103122

Author version available

Highly diastereoselective synthesis of imidazolidine-dispirooxindoles via three-component [3 + 2] cycloadditions of isatins, 2-(aminomethyl)pyridine and isatin-based imines

H. Zhao, X. Chen, Z. Yang, T. Tian, B. Li, W. Meng, X. Song and H. Pang, RSC Adv., 2015, 5, 103116 DOI: 10.1039/C5RA21995G

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