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Synthesis 2017; 49(14): 3171-3182
DOI: 10.1055/s-0036-1588995
DOI: 10.1055/s-0036-1588995
paper
Acid-Catalyzed Protocol for the Synthesis of Novel 6-Substituted Tetrahydroquinolines by Highly Regioselective C6-Functionalization of Tetrahydroquinolines with Chromene Hemiacetals or β-Nitrostyrenes
Weitere Informationen
Publikationsverlauf
Received: 02. März 2017
Accepted after revision: 18. März 2017
Publikationsdatum:
18. April 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201714/lookinside/thumbnails/ss-2017-n1647-op_10-1055_s-0036-1588995-1.jpg)
Abstract
A simple and novel method has been developed for the C6-functionalization of unprotected tetrahydroquinoline with chromenes or β-nitrostyrenes in aqueous medium to afford novel 6-substituted tetrahydroquinolines. This method is simple and convenient, and has low costs and mild reaction conditions. Regioselectively C6-alkylated products were obtained exclusively from tetrahydroquinoline, without the formation of C5-, C7-, C8-, or N-alkylated products.
Key words
tetrahydroquinolines - chromenes - nitrostyrenes - alkylation - electrophilic substitution - Friedel–Crafts reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588995.
- Supporting Information
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