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Communication | Special issue | Vol 5, No. 1, 1976, pp.213-221
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0213
Acid-catalyzed Reaction of 1-Substituted 10-Acetoxy-8-chloro-6-methoxy-2-methyl-7-oxo-Δ5,6,8,9-hexahydroisoquinolines

Hiroshi Hara, Osamu Hoshino, and Bunsuke Umezawa*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan

Abstract

Treatment with trifluoroacetic acid of the p-quinol acetates (VIa, b) derived from 1-benzyl-8-chlorotetrahydroisoquinolines (Va, b) gave the corresponding 8-chloromorphinandienones (VIIa, b), 1-chloroisopavines (VIIIa, b), and 4-β-hydroxyaporphines (IXa, b), respectively. By similar reactlon of p-quinol acetates (XIIIa-c), 8-chlorohomomorphinandienones (XIVa-c), 1-chlorohomoisopavines (XVa-c), and 4β-hydroxyhomoaporphines (XVIa, b) were yielded, respectively.