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Communication | Regular issue | Vol 20, No. 11, 1983, pp.2149-2154
Published online, 1st January, 1970
DOI: 10.3987/R-1983-11-2149
A Comment on Lead Tetraacetate Oxidation of Four Guiacol-type 1,2,3,4-Tetrahydroisoquinolines

Hiroshi Hara, Hiroshi Shinoki, Osamu Hoshino, and Bunsuke Umezawa

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


Lead tetraacetate oxidation of four guiacol-type tetrahydroisoquinolines (1a, 2a, 6, and 7a) in CH2Cl2 at 0 °C gave the respective o-quinol acetates (4a, 12, 8, and 13). On the other hand, oxidation of them in AcOH at room temperature afforded the acetoxy derivatives (14a, 3a, 9, and 14a), respectively. Treatment of the o-quinol acetate (4a, 12, 8, or 13) with AcOH yielded the same product (14a, 3a, 9, or 14a) as above. The o-quinol acetate (4a or 13) was thermally transformed into the 4-acetoxy derivative (5a or 15).