Application of Flow Chemistry to Macrocyclization of Crown Ethers

This paper reports a new continuous-flow synthesis of chiral and achiral pyridino-18-crown-6 ethers. Macrocyclizations have been performed in a packed-bed flow reactor where deprotonation of a bifunctional primary or a secondary alcohol takes place with potassium hydroxide as a heterogeneous base av...

Full description

Saved in:
Bibliographic Details
Published in:Journal of flow chemistry 2016-12, Vol.6 (4), p.297-301
Main Authors: Fődi, Tamás, Kupai, József, Túrós, György, Németh, Tamás, Rojik, Eszter, Riethmüller, Eszter, Balogh, György Tibor, Huszthy, Péter
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Green Chemistry
Industrial Chemistry/Chemical Engineering
Inorganic Chemistry
Nanochemistry
Organic Chemistry
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:This paper reports a new continuous-flow synthesis of chiral and achiral pyridino-18-crown-6 ethers. Macrocyclizations have been performed in a packed-bed flow reactor where deprotonation of a bifunctional primary or a secondary alcohol takes place with potassium hydroxide as a heterogeneous base avoiding the use of stronger and more dangerous one, sodium hydride. Ditosylate derivatives of pyridine as precursors for the macrocyclization used in batch condition were replaced by the appropriate diiodides and optimization of the parameters provided higher yields in shorter reaction times. The setup presented here is suitable for the preparation of different ethers by Williamsontype syntheses in continuous-flow reactions.
ISSN:2062-249X
2063-0212
DOI:10.1556/1846.2016.00033