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

Chisholm, D. R. and Zhou, G.-L. and Pohl, E. and Valentine, R. and Whiting, A. (2016) 'Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines.', Beilstein journal of organic chemistry., 12 . pp. 1851-1862.

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.

Item Type:Article
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Status:Peer-reviewed
Publisher Web site:http://dx.doi.org/10.3762/bjoc.12.174
Publisher statement:© 2016 Chisholm et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
Date accepted:12 July 2016
Date deposited:31 August 2016
Date of first online publication:16 August 2016
Date first made open access:No date available

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