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Synthesis of a novel pyrrolo-[3,2-c]quinoline N-oxide by aza-Baylis-Hillman adduct of o-nitrobenzaldehyde
Journal article   Open access   Peer reviewed

Synthesis of a novel pyrrolo-[3,2-c]quinoline N-oxide by aza-Baylis-Hillman adduct of o-nitrobenzaldehyde

Evelina Colacino, Christophe Andre, Jean Martinez and Frédéric Lamaty
Tetrahedron Letters, Vol.49, pp.4953-4955
2008

Abstract

Hexacyclic keto nitrone 3-Keto-pyrrole Ring closing metathesis (RCM) Aza-Baylis-Hillman (Aza-BH) Reductive cyclization Nitrone deoxygenation
A new and high yielding approach for the synthesis of a novel pyrrolo-[3,2-c]quinoline N-oxide is described. The key step consisted in the palladium-catalyzed reductive cyclization of an uncomon 3-ketopyrrole derivative of o-nitrobenzaldehyde, obtained in a straightforward manner through an aza-Baylis-Hillman/ring closing metathesis/aromatization reaction. A deoxygenation reaction of this novel pyrrolo-[3,2-c]quinoline N-oxide afforded a new substituted pyrrolo-[3,2-c]quinoline analogue.
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