Ohmic Heating-Assisted Synthesis of 3-Arylquinolin-4(1H)-ones by a Reusable and Ligand-Free Suzuki鈥揗iyaura Reaction in Water
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- 作者：Joana Pinto ; Vera L. M. Silva ; Ana M. G. Silva ; Lu铆s M. N. B. F. Santos ; Artur M. S. Silva
- 刊名：Journal of Organic Chemistry
- 出版年：2015
- 出版时间：July 2, 2015
- 年：2015
- 卷：80
- 期：13
- 页码：6649-6659
- 全文大小：507K
- ISSN：1520-6904
文摘
Potential bioactive 3-arylquinolin-4(1H)-ones were synthesized under ohmic heating using an efficient, reusable, and ligand-free protocol developed for the Suzuki鈥揗iyaura coupling of 1-substituted-3-iodoquinolin-4(1H)-ones with several boronic acids in water using Pd(OAc)2 as a catalyst and tetrabutylammonium bromide (TBAB) as the phase transfer catalyst. Good substrate generality, ease of execution, short reaction time, and practicability make this method exploitable for the generation of libraries of B ring-substituted 3-arylquinolin-4(1H)-ones. After a simple workup, the Pd/catalyst-H2O-TBAB system could be reused for at least seven cycles without significant loss of activity.