Synthesis of isoquinolines from benzylaminoacetonitriles. Part I. Compounds prepared from veratrylamine

Autor: R. D. Waigh, D. N. Harcourt
Rok vydání: 1971
Předmět:
Zdroj: Journal of the Chemical Society C: Organic. :967
ISSN: 0022-4952
DOI: 10.1039/j39710000967
Popis: 3,4-Dimethoxybenzylaminoacetonitriles cyclise in concentrated sulphuric acid to give, after hydrolysis, 1,2-dihydroisoquinolin-4(3H)-ones, in excellent yield. 3,3-Disubstituted 1,2-dihydroisoquinolin-4(3H)-ones are stable as the free base, in contrast to the 3-unsubstituted and 3-monosubstituted analogues. 1,2-Dihydro-6,7-dimethoxy-3-phenylisoquinolin-4(3H)-one as the free base underwent aerial oxidation to give 6,7-dimethoxy-3-phenylisoquinolin-4-ol, and could also be converted by a series of reactions into 6,7-dimethoxy-3-phenylisoquinoline in good yield.
Databáze: OpenAIRE