Imino Diels-Alder Reaction: Application to the Synthesis of Diverse Cyclopenta[c]Quinoline Derivatives

Helène Posson; Jean-Pierre Hurvois; Claude Moinet

doi:10.1055/s-2000-6487

Synlett 2000; 2000(2): 209-212
DOI: 10.1055/s-2000-6487

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Imino Diels-Alder Reaction: Application to the Synthesis of Diverse Cyclopenta[c]Quinoline Derivatives

Helène Posson^* , Jean-Pierre Hurvois, Claude Moinet

^*Laboratoire d'Electrochimie, et d'Organometalliques, UMR 6509, Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France; Fax +33 2 99 28 16 60; E-mail: Jean-Pierre.Hurvois@univ-rennes1.fr

Abstract

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Several unreported tetrahydrocyclopenta[c]quinoline derivatives have been prepared employing an imino Diels-Alder cycloaddition as the key ring forming step. The tetrahydroquinoline 10 can be directly oxidized into the cyanoamine 15 which upon treatment with LDA and propyl bromide is easily converted into the propyl derivative. On direct treatment with NaBH₄ in methanol the reductive decyanation occurred, leading stereospecifically to 17.

imino Diels-Alder cyclocondensation - cyclopenta[c] quinoline - electrochemistry - anodic cyanation

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