ortho-Dienone synthesis by the phenolic oxidation of dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline

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Abstract
Oxidation of 1,2,3,4-tetrahydro-7-hydroxy-1-(2-hydroxy-4-methoxyphenethyl)-6-methoxy-2-methylisoquinoline (III) and its methoxy-analogue (IV) with ferric chloride gave ortho-dienone-type homoproaporphines [(Va) and (VIa), respectively]. The mass spectral patterns of the ortho-dienones [(Va) and (VIa)] are also discussed.