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Letters in Organic Chemistry

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

DOI: 10.2174/15701786113109990045

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

Page: [640 - 644] Pages: 5

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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.