A New Route to Acridines: Pauson-Khand Reaction on Quinoline-Bearing 1-En-7-ynes Leading to Novel Tetrahydrocyclopenta[c]acridine-2,5-diones



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Synthesis 2005, 2400-2406.

 Patin, A., Belmont, P.

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: Dr. Philippe Belmont


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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