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
R = H, Ph
N
- alkylation of the amide with the appropriate alkynyl or alkenyl halides afforded the key intermediate for cyclisation
Diels - Alder cyclisations
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
