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. 2013 May 3;18(5):5142-54.
doi: 10.3390/molecules18055142.

A facile synthesis of functionalized dispirooxindole derivatives via a three-component 1,3-dipolar cycloaddition reaction

Jun He  1 , Guang Ouyang, Zhixiang Yuan, Rongsheng Tong, Jianyou Shi, Liang Ouyang
Affiliations

A facile synthesis of functionalized dispirooxindole derivatives via a three-component 1,3-dipolar cycloaddition reaction

Jun He et al. Molecules. .

Abstract

An efficient synthesis of novel dispirooxindoles has been achieved through three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the decarboxylative condensation of isatin and an α-amino acid with the dipolarophile 5-benzylideneimidazolidine-2,4-dione. The improved procedure features mild reaction conditions, high yields, high diastereoselectivities, a one-pot procedure and operational simplicity.

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Figures

Scheme 1
Scheme 1
The synthetic route to compounds 3.
Scheme 2
Scheme 2
Possible reaction mechanism for the synthesis of dispirooxindole hydantoin derivatives.
Scheme 3
Scheme 3
MCRs of thioproline 2b.
Figure 1
Figure 1
(a) Selected 1H- and 13C-NMR chemical shifts of 4b. (b) Single crystal X-ray diffraction study of compound 4b.
Scheme 4
Scheme 4
Plausible mechanism for the formation of compound 4.
See this image and copyright information in PMC

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