Issue 21, 2015
From the journal:

Organic & Biomolecular Chemistry

Convenient synthesis of functionalized spiro[indoline-3,2′-pyrrolizines] or spiro[indoline-3,3′-pyrrolidines] via multicomponent reactions†

Jing Sun,a   Liang Chen,a   Hui Gonga  and  Chao-Guo Yan*a  

* Corresponding authors

a College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China
E-mail: cgyan@yzu.edu.cn
Fax: +86-514-87975244
Tel: +86-514-8797531

Abstract

A general and practical route for the in situ generation of a new type of azomethine ylide and its sequential 1,3-dipolar cycloaddition reaction was successfully established. The three-component reaction of secondary α-amino acids including proline, sarcosine, thiazolidine-4-carboxylic acid with dialkyl acetylenedicarboxylate and 3-methyleneoxindoles in refluxing ethanol afforded the functionalized spiro[indoline-3,2′-pyrrolizines], spiro[indoline-3,3′-pyrrolidines] and spiro[indoline-3,6′-pyrrolo[1,2-c]thiazoles] in good yields and with high diastereoselectivity. Furthermore, similar multicomponent reactions using primary α-amino acids such as glycine, alanine and phenylalanine resulted in the corresponding (spiro[indoline-3,3′-pyrrolidine]-1′-yl)maleates.

Graphical abstract: Convenient synthesis of functionalized spiro[indoline-3,2′-pyrrolizines] or spiro[indoline-3,3′-pyrrolidines] via multicomponent reactions

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Article information

DOI
https://doi.org/10.1039/C5OB00437C
Article type
Paper
Submitted
05 Mar 2015
Accepted
02 Apr 2015
First published
03 Apr 2015

Org. Biomol. Chem., 2015,13, 5905-5917

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Convenient synthesis of functionalized spiro[indoline-3,2′-pyrrolizines] or spiro[indoline-3,3′-pyrrolidines] via multicomponent reactions

J. Sun, L. Chen, H. Gong and C. Yan, Org. Biomol. Chem., 2015, 13, 5905 DOI: 10.1039/C5OB00437C

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