Synthesis of pyridoquinolines (2)

An anomalous Reissert reaction between quinoline and benzoyl chloride gave a synthetically useful N - benzoyl cinnamaldehyde, which was readily converted into the required hydrazone
poster 5a

R = H, Ph

N - alkylation of the amide with the appropriate alkynyl or alkenyl halides afforded the key intermediate for cyclisation
poster 5b

Diels - Alder cyclisations
poster 5c

The propargyl chloride derivative has failed to cyclise under thermal and Lewis acid conditions
Note that the cinnamyl bromide derived product has not fully aromatised, as predicted by the reaction mechanism

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