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

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

Volume: 10 Issue: 9

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

Affiliation:

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

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.

Cite this article as:

Radchatawedchakoon Widchaya, Promthong Niwat and Sakee Uthai, First Synthesis of 5- and 7-Phenylethynyl-8-hydroxyquinolines by Sonogashira Reaction, Letters in Organic Chemistry 2013; 10 (9) . https://dx.doi.org/10.2174/15701786113109990045