Potentiell ZNS-wirksame,tricyclische Verbindungen mit verbrücktem Mittelring, 1. Mitt. Umsetzung von Benzo[c]furanen mit Dehydrobenzol

Potential ZNS-effective, tricyclic compounds with a bridged middle ring, I: Reaction of benzo[c]furans with benzyne The preparation of 9,10-epoxy-9,10-dihydroanthracene derivatives with basic side chains, potential psychotherapeutics, has been investigated. 1,4-Epoxy-1,2,3,4-tetrahydronaphthalenes containing protected carbonyl groups at C–1 were synthesized from furan derivatives by Diels-Alder reaction with benzyne and then by hydrogenation. 1-Diethoxymethylbenzo[c]furan was formed by flash vacuum thermolysis and underwent renewed cycloaddition with benzyne to yield 9-diethoxymethyl-9,10-epoxy-9,10-dihydroanthracene. The regeneration of the carbonyl group, required for the introduction of the basic side chain, could however only be achieved with simultaneous opening of the ether function.