1,3-Dipolar cycloaddition reaction for diastereoselective synthesis of functionalized dihydrospiro[indoline-3,2＇-pyrroles]

The BF_3OEt_2 catalyzed one-pot 1,3-dipolar cycloaddition reaction of benzylamines,isatins and dimethyl acetylenedicarboxylate in dry methylene dichloride afforded the functionalized dihydrospiro[indoline-3,2＇-pyrroles]in moderate to good yields and with high diastereoselectivity.The reaction was ac...

Full description

Saved in:
Bibliographic Details
Published in:Chinese chemical letters 2017-02, Vol.28 (2), p.329-332
Main Authors: Wu, Ping, Gao, Hong, Sun, Jing, Yan, Chao-Guo
Format: Article
Language:English
Subjects:
1,3-Dipolar cycloaddition
Azomethine ylide
Electron-deficient alkyne
One-pot reaction
Spiro[indoline-3,2′-pyrrole]
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The BF_3OEt_2 catalyzed one-pot 1,3-dipolar cycloaddition reaction of benzylamines,isatins and dimethyl acetylenedicarboxylate in dry methylene dichloride afforded the functionalized dihydrospiro[indoline-3,2＇-pyrroles]in moderate to good yields and with high diastereoselectivity.The reaction was accomplished by the tandem 1,3-dioplar cycloaddition of in situ generated azomethine ylide with acetylenedicarboxylate and the nucleophilic addition of pyrrole ring to second molecular acetylenedicarboxylate.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2016.07.016