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Preparation of 7,8-dimethoxy-3,4-dihydroisoquinoline, facile route to 7,8-dioxygenated-3,4-dihydroisoquinolines

โœ Scribed by A. M. El-Fishawy; D. J. Slatkin; J. E. Knapp; P. L. Schiff Jr.

Publisher
John Wiley and Sons
Year
1984
Tongue
English
Weight
264 KB
Volume
73
Category
Article
ISSN
0022-3549

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โœฆ Synopsis

Oxidation of 7,8-dimethoxy-l,2,3,4-tetrahydroisquinoline with potassium permanganate in acetone afforded 7,8-dimethoxy-3,4-dihydroisoquinoline as the primary product. Hence, oxidation of the appropriate secondary nonphenolic 7,8-dioxygenated tetrahydroisoquinoline alkaloid is thus a facile method for the generation of the corresponding imine. The imine is not easily prepared oia the usual synthetic route involving ring closure of P-phenethylamine derivatives.

Keyphrases n 7.8-Dimethoxy-1,2,3.4-tetr~hydroisquinoline-oxidation with potassium permanganate 0 7.8-Dimethoxy-3.4-dihydroisoquinoline-synthesis, secondary amine, oxidation with potassium permanganate 0 7.8-Dioxygenated-3,4-dihydroisoquinoline-secondary amine, oxidation with potassium permanganate ' Hyland PDQ Laser Nephelometer. Northbrook. 111.

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In an attempt to ascertain the scope of using ethyl polyphosphate in the Bischler-Napieralsky annelation reaction, a title compound was synthesized and reduced to the respective 1-(3,4-dimethoxyphenylmethyl)-3-phenyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline.