Combes Quinoline Synthesis Mechanism | Organic Chemistry @OrganicMechanismsChannel

Uploaded August 2021 | Updated September 2026, 1 week ago

The mechanism for a Combes reaction which involves first a condensation of an arylamine with a 1,3-diketone, keto-aldehyde or dialdehyde in order to produce an enamine. This is then followed by cyclodehydration to yield the quinoline product. Multiple mechanisms for this reaction have been put forward. It was initially proposed that cyclization to linear products was due to initial protonation of a more reactive site on the aromatic ring, thus, blocking cyclization to angular products. However, this was proven to not be the case. Rather, condensation of an aniline with a dione with loss of water provides enamine. This is followed by ketone protonation and subsequent cyclization.

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Combes Quinoline Synthesis Mechanism | Organic Chemistry

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