Condensed heteroaromatic ring systems. IX Total synthesis of aaptamine.

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Abstract
A five-step synthesis of aaptamine, a marine alkaloid containing a benzo[d, e][1, 6]naphthyridine ring, from 6, 7-dimethoxy-8-nitro-1(2H)-isoquinolone was accomplished in satisfactory yield. As a basis for the above synthesis, a facile preparation of 6, 7-dimethozy-1(2H)-isoquinolones from 3, 4-dimethoxybenzaldehydes was developed using the palladium-catalyzed reaction of o-bromobenzaldehyde derivatives with trimethylsilylacetylene as a key reaction.

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