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.
Letters in Organic Chemistry
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.
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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
DOI https://dx.doi.org/10.2174/15701786113109990045 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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