Abstract
Lithiation of 4-acetyl 2-chloro pyridine ethylene glycol ketal by exchange with lithium diisopropylamine (LDA) led to 4-acetyl 2-chloro 3-lithio pyridine ethylene glycol ketal. This lithio derivative was reacted with aromatic aldehydes giving the expected alcohols, which were reduced by triethylsilane and trifluoroacetic acid at room temperature. The resulting 4-acetyl 3-arylmethyl 2-chloro pyridine ethylene glycol ketals were hydrolysed and cyclized in acidic medium, leading to polycondensed heterocyclic systems that have a 1-chloro 5-methyl isoquinoline nucleus fused by its [g] bond to the starting aromatic aldehyde.
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