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Synthesis 2005(14): 2400-2406  
DOI: 10.1055/s-2005-870016
PAPER
© 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;
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Publication History

Received 30 March 2005
Publication Date:
13 July 2005 (online)

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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

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Diphenylamine derivatives are constructed via the Ullman reaction.

20

Observation made by the analysis of the 1NMR spectra, showing only one diastereomer (trans/cis ratio > 95:5).

21

These results were correlated with other studies from the literature, see ref. 16a, 19.