Issue 9, 2016

Pd catalyzed facile synthesis of cyclopenta[b]quinolin-1-one via sequential Sonogashira coupling and annulation. An unusual mode of ring closure, using sulphur as a soft nucleophile

Abstract

Pd mediated one pot sequential Sonogashira coupling followed by annulation using o-alkynyl aldehyde is reported. Contrary to the established modes of ring closures, an unusual mode of the initial attack of sulphur across the triple bond occurs leading to a cascade of reactions. The protocol requires just single column chromatography, delivering cyclopenta[b]quinolin-1-one in high yields. Furthermore chemoselective transformations were carried out across annulated precursors.

Graphical abstract: Pd catalyzed facile synthesis of cyclopenta[b]quinolin-1-one via sequential Sonogashira coupling and annulation. An unusual mode of ring closure, using sulphur as a soft nucleophile

Supplementary files

Article information

Article type
Research Article
Submitted
13 May 2016
Accepted
04 Jul 2016
First published
05 Jul 2016

Org. Chem. Front., 2016,3, 1100-1104

Pd catalyzed facile synthesis of cyclopenta[b]quinolin-1-one via sequential Sonogashira coupling and annulation. An unusual mode of ring closure, using sulphur as a soft nucleophile

R. M. Singh, R. Kumar, K. C. Bharadwaj and T. Gupta, Org. Chem. Front., 2016, 3, 1100 DOI: 10.1039/C6QO00203J

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