A. Qandil
Dec 1, 1999
Citations
0
Influential Citations
7
Citations
Journal
Synthesis
Abstract
The cyclic ketone, 6,7-dimethoxy-2-tetralone, a versatile starting material for many dopaminergic compounds, can be pre- pared practically, cost-effectively and in good overall yield. The synthesis starts from readily available 3,4-dimethoxyphenylacetic acid. Ring iodination gave the 2-iodo-4,5-dimethoxy acid, which was converted to its methyl ester. Palladium (II)-catalyzed Heck cross coupling afforded the expected unsaturated diester, which was then catalytically hydrogenated. Dieckmann condensation, fol- lowed by careful decarboxylation led to the desired 2-tetralone. Re- agents used in subsequent reactions are inexpensive and readily available. This method appears practical for large-scale synthesis of the target tetralone, compared with other procedures reported in the literature.