Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

Chisholm, D.R.; Zhou, G.-L.; Pohl, E.; Valentine, R.; Whiting, A.

doi:10.3762/bjoc.12.174

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines Thumbnail

Authors

D.R. Chisholm

G.-L. Zhou

Professor Ehmke Pohl ehmke.pohl@durham.ac.uk
Professor

R. Valentine

Professor Andrew Whiting andy.whiting@durham.ac.uk
Professor

Abstract

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.

Citation

Chisholm, D., Zhou, G., Pohl, E., Valentine, R., & Whiting, A. (2016). Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines. Beilstein Journal of Organic Chemistry, 12, 1851-1862. https://doi.org/10.3762/bjoc.12.174

Journal Article Type	Article
Acceptance Date	Jul 12, 2016
Online Publication Date	Aug 16, 2016
Publication Date	Aug 16, 2016
Deposit Date	Aug 28, 2016
Publicly Available Date	Aug 31, 2016
Journal	Beilstein Journal of Organic Chemistry
Print ISSN	1860-5397
Publisher	Beilstein-Institut
Peer Reviewed	Peer Reviewed
Volume	12
Pages	1851-1862
DOI	https://doi.org/10.3762/bjoc.12.174

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Copyright Statement
© 2016 Chisholm et al.; licensee Beilstein-Institut.<br /> This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.<br /> The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)