PAPER	Synthesis 2005: 2400-2406   DOI: 10.1055/s-2005-870016
© Georg Thieme Verlag Stuttgart · New York
A New Route to Acridines: Pauson-Khand Reaction on Quinoline-Bearing 1-En-7-ynes Leading to Novel Tetrahydrocyclopenta[c]acridine-2,5-diones
Amaury Patin, Philippe Belmont*
Université Claude Bernard, Lyon I. UMR CNRS 5181, Méthodologie de Synthèse et Molécules Bioactives, Bâtiment CPE, 43 boulevard du 11 Novembre 1918, 69622 Villeurbanne cedex, France Fax: +33(472)432963; e-Mail: belmont@cpe.fr;
Received 30 March 2005

Abstract

Efficient Pauson-Khand reactions on quinolines bearing 1-en-7-ynes features gave tetrahydrocyclopenta[c]acridine derivatives. The quinoline intermediates were obtained in two steps: a Sonogashira reaction with functionalized alkynes (TMS, Bu, Ph, CHB₂OTHP) followed by a Grignard reaction with allylmagnesium bromide. The sequence provides new acridine structures in four high yielding steps from commercially available quinolines.

Key words

quinoline - acridine - enynes - intramolecular Pauson-Khand reaction - cyclopenta[c]acridine