4-Substituted 6,7-dimethoxyisoquinolines

4-Methyl- and 4-ethyl-6,7-dimethoxyisoquinolines have been synthesized by base-induced alkylation of homoveratronitrile, hydrogenation, N-formylation of the resultant amines, phosphorus pentoxide-induced cyclization and palladium-catalyzed dehydrogenation. Homoveratronitrile underwent self-condensat...

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Bibliographic Details
Published in:Canadian journal of chemistry 1968-04, Vol.46 (7), p.1160-1163
Main Authors: Wenkert, Ernest, Haugwitz, R. D
Format: Article
Language:English
Online Access:Get full text
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Summary:4-Methyl- and 4-ethyl-6,7-dimethoxyisoquinolines have been synthesized by base-induced alkylation of homoveratronitrile, hydrogenation, N-formylation of the resultant amines, phosphorus pentoxide-induced cyclization and palladium-catalyzed dehydrogenation. Homoveratronitrile underwent self-condensation to the dimer, 2,4-bis-(3,4-dimethoxyphenyl-)3-aminocrotonitrile, under the influence of potassium t-butoxide. 4-Carbomethoxy-6,7-dimethoxyisoquinoline was synthesized by the following sequence of reactions: base-catalyzed condensation of homoveratronitrile with ethyl formate, acid-induced interaction with urethane, pyrolytic cyclization, phosphorus oxychloride treatment, palladium-catalyzed hydrogenolysis, and hydrolysis and esterification of the resultant 4-cyano-6,7-dimethoxyisoquinoline.
ISSN:0008-4042
1480-3291
DOI:10.1139/v68-195