Chisholm DR1, Zhou GL1, Pohl E2, Valentine R3, Whiting A1.
Beilstein J Org Chem. 2016 Aug 16;12:1851-1862. eCollection 2016.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. Read More