Issue 33, 2016

Facile construction of novel imidazolidine-spirooxindoles via diastereoselective cycloaddition of N-acylhydrazine-derived imines with 3-isothiocyanato oxindoles

Abstract

In the presence of 10 mol% of Na2CO3, the desired imidazolidine-spirooxindoles were obtained in 81–99% yield with up to 99 : 1 dr by means of the diastereoselective [3 + 2] cycloaddition of N-acylhydrazine-derived imines with 3-isothiocyanato oxindoles. Single-crystal X-ray structure analysis was conducted to determine the relative stereochemistry of the imidazolidine-spirooxindoles. Diastereoselective access to the imidazolidine-spirooxindoles was hypothesized by the proposed mechanism.

Graphical abstract: Facile construction of novel imidazolidine-spirooxindoles via diastereoselective cycloaddition of N-acylhydrazine-derived imines with 3-isothiocyanato oxindoles

Supplementary files

Article information

Article type
Paper
Submitted
22 Jan 2016
Accepted
07 Mar 2016
First published
10 Mar 2016

RSC Adv., 2016,6, 27690-27695

Facile construction of novel imidazolidine-spirooxindoles via diastereoselective cycloaddition of N-acylhydrazine-derived imines with 3-isothiocyanato oxindoles

H. Zhao, B. Li, T. Tian, X. Song, H. Pang, X. Chen, Z. Yang and W. Meng, RSC Adv., 2016, 6, 27690 DOI: 10.1039/C6RA01962E

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