Publication details for Prof. Ehmke PohlChisholm, D. R., Zhou, G.-L., Pohl, E., Valentine, R. & Whiting, A. (2016). Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines. Beilstein Journal of Organic Chemistry 12: 1851-1862.
- Publication type: Journal Article
- ISSN/ISBN: 1860-5397 (electronic)
- DOI: 10.3762/bjoc.12.174
- Further publication details on publisher web site
- Durham Research Online (DRO) - may include full text
Author(s) from Durham
The synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisation. A versatile and stable quinolin-2-one intermediate was identified, which could be reduced to the corresponding THQ with borane reagents, or to the DHQ with diisobutylaluminium hydride via a novel elimination that is more favourable at higher temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence.