Paper
Electrochemical oxidation of aromatic ethers. Part 6. Oxidation of 4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline and attempted synthesis of 4-(3,4-dimethoxybenzyl)6,7-dimethoxy-2-methyl-1,4-dihydro-3(2H)-isoquinolone
Published 1980 · M. Carmody, M. Sainsbury, R. Newton
Journal of The Chemical Society-perkin Transactions 1
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Abstract
The cyclisation of 3-(3,4-dimethoxyphenyl)-2-(2-hydroxymethyl-4,5-dimethoxyphenyl)-N-methylpropionamide (5) and related compounds does not yield 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,4-dihydro-3(2H)isoquinolone, but gives instead dibenzo[b,f]cycloheptane derivatives. Anodic oxidation of 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline affords the corresponding 3,4-dihydroisoquinolinium and 4-(3,4-dimethoxybenzylidene)-6,7-dimethoxy-2-methyl-1,4-dihydroisoquinolinium salts. No intramolecularly aryl-aryl coupled products are isolated and the implication of this result on the design of substrates for the synthesis of biphenyl derivatives is discussed.
Electrochemical oxidation of aromatic ethers yields 3,4-dihydroisoquinolinium and 4-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,4-dihydro-3(2H)-isoquinolone, but
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