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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

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

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]

PMID: 27829891

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