Issue 6, 2015
From the journal:

RSC Advances

Construction of dispirocyclohexyl-3,3′-bisoxindole and dispirocyclopentyl-3,3′-bisoxindole via domino cycloaddition reactions of N-benzylbenzimidazolium salts with 2-(2-oxoindolin-3-ylidene)acetates†

Guo-Liang Shen,a   Jing Suna  and  Chao-Guo Yan*a  

* Corresponding authors

a College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China
E-mail: cgyan@yzu.edu.cn

Abstract

The cycloaddition reaction of N-benzyl-N-phenacylbenzimidazolium salts with two molecules of 2-(2-oxoindolin-3-ylidene)acetate in ethanol in the presence of triethylamine as base afforded functionalized dispirocyclohexyl-3,3′-bisoxindoles in good yields. Alternatively, the similar reaction of N-benzyl-N-(alkoxycarbonylmethyl)benzimidazolium salts with two molecules of 2-(2-oxoindolin-3-ylidene)acetate resulted in dispirocyclopentyl-3,3′-bisoxindole derivatives in good yields and with high diastereoselectivity.

Graphical abstract: Construction of dispirocyclohexyl-3,3′-bisoxindole and dispirocyclopentyl-3,3′-bisoxindole via domino cycloaddition reactions of N-benzylbenzimidazolium salts with 2-(2-oxoindolin-3-ylidene)acetates

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Article information

DOI
https://doi.org/10.1039/C4RA13760D
Article type
Communication
Submitted
04 Nov 2014
Accepted
08 Dec 2014
First published
08 Dec 2014

RSC Adv., 2015,5, 4475-4483

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Construction of dispirocyclohexyl-3,3′-bisoxindole and dispirocyclopentyl-3,3′-bisoxindole via domino cycloaddition reactions of N-benzylbenzimidazolium salts with 2-(2-oxoindolin-3-ylidene)acetates

G. Shen, J. Sun and C. Yan, RSC Adv., 2015, 5, 4475 DOI: 10.1039/C4RA13760D

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