Studies on quinolizinium salts—VII : The acid-catalysed reaction of acrolein and malonaldehyde with aniline

Add time:09/24/2019    Source:sciencedirect.com

Hydrogen bromide-catalysed reaction of acrolein, malonaldehyde, paraformaldehyde and acetaldehyde with aniline was investigated in connection with the mechanism proposed for the quinolizinium bromide (I)-aniline reaction. Acrolein undergoes retrograde aldol-like fragmentation possibly with the formation of N-ethylidene and N-methyleneaniline (XX and XXI), together with cyclization to quinoline derivatives (II–IV). The add-catalysed reaction of XV is also shown to proceed with fragmentation to give possible fragments (XXI and XXVII). Apparently the fragments (XX, XXI and XXVII) yield many products which are produced from paraformaldehyde and acetaldehyde under similar conditions.

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