Preparation of Polycyclic Azaarenes by an Extended Pomeranz-Fritsch Procedure

 

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Abstract

An extension of the Pomeranz-Fritsch procedure has been evaluated as a route to some polycyclic azaarenes. Aromatic aldehydes were treated with the dimethyl and diethyl acetals of 2-aminoethanal, the resulting imines reduced to amines which were tosylated and the resulting sulfonamides treated under a range of acidic conditions. The two naphthaldehydes led to benzo[f]isoquinoline and benzo[h]isoquinoline in overall yields of 13% and 36%. Phenanthrene-9-carbaldehyde and phenanthrene-3-carbaldehyde gave dibenzo[f,h]isoquinoline and naphtho[2,1-g]isoquinoline, respectively, as the major tetracyclic products. No pentacyclic product was obtained from a similar sequence starting from pyrene-1-carbaldehyde.

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