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

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.

SUBMITTER: Chisholm DR 

PROVIDER: S-EPMC5082455 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature