Synthesis 2015; 47(13): 1851-1860
DOI: 10.1055/s-0034-1380496
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Quinolin-4(1H)-one Derivatives by a Sequential Michael Addition–Elimination/Palladium-Catalyzed Buchwald–Hartwig Amination Reaction

Yinghua Wang
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China   Email: jspeng1998@nefu.edu.cn   Email: 080122@nefu.edu.cn
,
Hanyu Liang
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China   Email: jspeng1998@nefu.edu.cn   Email: 080122@nefu.edu.cn
,
Chunxia Chen*
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China   Email: jspeng1998@nefu.edu.cn   Email: 080122@nefu.edu.cn
,
Deqiang Wang
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China   Email: jspeng1998@nefu.edu.cn   Email: 080122@nefu.edu.cn
,
Jinsong Peng*
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China   Email: jspeng1998@nefu.edu.cn   Email: 080122@nefu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 06 January 2015

Accepted after revision: 03 March 2015

Publication Date:
26 March 2015 (online)


Abstract

A convenient approach has been developed for the construction of quinolin-4(1H)-one frameworks, starting from (Z)-β-chlorovinyl aromatic ketones and amines. Intermolecular Michael addition of an amine to a (Z)-β-chlorovinyl ketone was followed by elimination of a chloride anion to give enamine intermediates, with full retention of the initial Z-configuration. The enamine intermediates were transformed into quinolin-4(1H)-one products by a palladium-catalyzed intramolecular N-arylation in a tandem one-pot manner, with good to excellent yields.

Supporting Information