First Synthesis of 5- and 7-Phenylethynyl-8-hydroxyquinolines by Sonogashira Reaction

Author(s): Widchaya Radchatawedchakoon, Niwat Promthong, Uthai Sakee.

Journal Name: Letters in Organic Chemistry

Volume 10 , Issue 9 , 2013

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Abstract:

5-Chloro-7-(2-phenylethynyl)quinolin-8-ol and 7-iodo-5-(2 -phenylethynyl)quinolin-8-ol was synthesized by Pd-CuI catalyzed Sonogashira-type cross-coupling of 8-(benzyloxy)-5-chloro-7-iodoquinoline and 8-(benzyloxy)-5,7- diiodoquinoline with 1-ethynylbenzene. The coupling products were smoothly debenzylated by boron trichloride in dichloromethane to afford the corresponding products in good yields.

Keywords: Sonogashira, Coupling, Ethynylbenzene, Quinoline, Palladium.

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Article Details

VOLUME: 10
ISSUE: 9
Year: 2013
Page: [640 - 644]
Pages: 5
DOI: 10.2174/15701786113109990045
Price: $65

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