Studies on the syntheses of heterocyclic compounds. Part CCLXXXI. Synthesis of homoprotoberberine-type compounds by phenolic cyclisation
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 6,p. 874-878
- https://doi.org/10.1039/j39690000874
Abstract
The phenolic cyclisation of 1,2,3,4-tetrahydro-1-(3-hydroxy-4-methoxyphenethyl)-6,7-dimethoxyisoquinoline (VI) gave the homoprotoberberine-type compound (VII), in which cyclisation had taken place at the ortho-position to the hydroxy-group. The suggested structure for the compound, (VII), was assigned from spectroscopic results; the synthesis of the compound supported the suggested structure. A Mannich reaction of (VI) however, afforded a normal reaction product, homoprotoberberine (XV).Keywords
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