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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
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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
Full article available at:
Thieme-connect.com>>
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Updated 18 Jan 2006
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