Ontology highlight
ABSTRACT:
SUBMITTER: Chisholm DR
PROVIDER: S-EPMC5082455 | biostudies-literature | 2016
REPOSITORIES: biostudies-literature
Chisholm David R DR Zhou Garr-Layy GL Pohl Ehmke E Valentine Roy R Whiting Andrew A
Beilstein journal of organic chemistry 20160816
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 te ...[more]