Phase‐Transfer Catalytic Strategy: Rapid Synthesis of Spiro‐Fused Heterocycles, Integrated with Four Pharmacophores‐Succinimide, Pyrrolidine, Oxindole, and Trifluoromethyl Group

An efficient and practical 1,3‐dipolar [3+2] cycloaddition of N‐2,2,2‐trifluoroethylisatin ketimines and maleimides has been achieved through phase‐transfer catalytic process by using the cheap quaternary ammonium salt as a catalyst. The strategy grants rapid generation of various complex trifluorom...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2021-02, Vol.2021 (5), p.788-793
Main Authors: Chen, Zheng‐Jun, Liang, Wei, Chen, Zhuo, Chen, Lin
Format: Article
Language:English
Subjects:
[3+2] Cycloaddition
Ammonium salts
Catalysts
Chemical synthesis
Cross coupling
Cycloaddition
Heterocycles
Imines
Phase-transfer catalysis
Quaternary ammonium salts
Rapid synthesis
Reaction mechanisms
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:An efficient and practical 1,3‐dipolar [3+2] cycloaddition of N‐2,2,2‐trifluoroethylisatin ketimines and maleimides has been achieved through phase‐transfer catalytic process by using the cheap quaternary ammonium salt as a catalyst. The strategy grants rapid generation of various complex trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s in good yields and with excellent diastereoselectivities. The preparative‐scale reaction in conjunction with the optimized Suzuki–Miyaura cross‐coupling derivatizations of the product give prominence to application prospect of this methodology. The investigation on the reaction mechanism implies that the real catalyst in the cycloaddition might be tetrahexylammonium carbonate. A phase‐transfer catalytic 1,3‐dipolar [3+2] cycloaddition grants rapid generation of various trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s that might be of great utility for drug discovery. The gram‐scale reaction in conjunction with the derivatizations of the product demonstrate the synthetic potential of this methodology. The reaction mechanism is also discussed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202001409