Issue 67, 2014

Mechanochemical milling promoted solvent-free imino Diels–Alder reaction catalyzed by FeCl3: diastereoselective synthesis of cis-2,4-diphenyl-1,2,3,4-tetrahydroquinolines

Abstract

Under mechanochemical ball-milling at room temperature, FeCl3 promoted Diels–Alder cycloaddition of styrene with in situ generated N-aryl aldimines in the absence of any solvent afforded exclusively cis-2,4-diphenyltetrahydroquinolines in good to excellent yields within 90 minutes. The isolation work up just involves washing the resulting reaction mixture with water and recrystallization from EtOH–H2O. The advantages of high diastereoselectivity, short reaction time, free use of organic solvent, low cost, employment of cheap, easily available and nontoxic catalyst, and simple work-up procedure make this protocol a very efficient and green alternative to traditional methods for constructing these kinds of heterocyclic skeletons.

Graphical abstract: Mechanochemical milling promoted solvent-free imino Diels–Alder reaction catalyzed by FeCl3: diastereoselective synthesis of cis-2,4-diphenyl-1,2,3,4-tetrahydroquinolines

Supplementary files

Article information

Article type
Communication
Submitted
03 Jun 2014
Accepted
29 Jul 2014
First published
04 Aug 2014

RSC Adv., 2014,4, 35635-35638

Author version available

Mechanochemical milling promoted solvent-free imino Diels–Alder reaction catalyzed by FeCl3: diastereoselective synthesis of cis-2,4-diphenyl-1,2,3,4-tetrahydroquinolines

Y. Tan, Z. Zhang, F. Wang, H. Wu and Q. Li, RSC Adv., 2014, 4, 35635 DOI: 10.1039/C4RA05252H

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