Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

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

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
• Public URL: https://durham-repository.worktribe.com/output/1377309