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. 2018 Feb 2;8(11):5702-5713.
doi: 10.1039/c7ra13207g.

Green synthesis of new pyrrolidine-fused spirooxindoles via three-component domino reaction in EtOH/H2O

Yong-Chao Wang  1 , Jun-Liang Wang  2 , Kevin S Burgess  3 , Jiang-Wei Zhang  4 , Qiu-Mei Zheng  1 , Ya-Dan Pu  1 , Li-Jun Yan  1 , Xue-Bing Chen  5
Affiliations

Green synthesis of new pyrrolidine-fused spirooxindoles via three-component domino reaction in EtOH/H2O

Yong-Chao Wang et al. RSC Adv. .

Abstract

An efficient, green and sustainable approach for the synthesis of novel polycyclic pyrrolidine-fused spirooxindole compounds was developed. The synthesis included a one-pot, three-component, domino reaction of (E)-3-(2-nitrovinyl)-indoles, isatins and chiral polycyclic α-amino acids under catalyst-free conditions at room temperature in EtOH-H2O. The salient features of this methodology are eco-friendliness, high yields and the ease of obtaining target compounds without the involvement of toxic solvents and column chromatography. These novel polycyclic pyrrolidine-fused spirooxindoles provide a collection of structurally diverse compounds that show promise for future bioassays and medical treatments.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Selected representative biologically active heterocycles and target compounds that exhibit pharmacological activities.
Fig. 2
Fig. 2. The diversity of reagents (5 and 6).
Scheme 1
Scheme 1. Proposed reaction mechanism for the synthesis of 4 and 8.
Fig. 3
Fig. 3. Single crystal X-ray diffraction study of compound 4c.
See this image and copyright information in PMC

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