Ohmic Heating-Assisted Synthesis of 3-Arylquinolin-4(1H)-ones by a Reusable and Ligand-Free Suzuki-Miyaura Reaction in Water

Joana Pinto; Vera L M Silva; Ana M G Silva; Luís M N B F Santos; Artur M S Silva

doi:10.1021/acs.joc.5b00793

Ohmic Heating-Assisted Synthesis of 3-Arylquinolin-4(1H)-ones by a Reusable and Ligand-Free Suzuki-Miyaura Reaction in Water

J Org Chem. 2015 Jul 2;80(13):6649-59. doi: 10.1021/acs.joc.5b00793. Epub 2015 Jun 17.

Authors

Joana Pinto, Vera L M Silva, Ana M G Silva¹, Luís M N B F Santos², Artur M S Silva

Affiliations

¹ ‡UCIBIO/REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal.
² §Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua Campo Alegre 687, 4169-007 Porto, Portugal.

PMID: 26035736
DOI: 10.1021/acs.joc.5b00793

Abstract

Potential bioactive 3-arylquinolin-4(1H)-ones were synthesized under ohmic heating using an efficient, reusable, and ligand-free protocol developed for the Suzuki-Miyaura 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.