Formation and reaction of o-quinol acetates of N-acyl- and N-methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols

被引：8

作者：

Hoshino, O ^{[1
]}

Suzuki, M ^{[1
]}

Ogasawara, H ^{[1
]}

机构：

[1] Sci Univ Tokyo, Fac Pharmaceut Sci, Shinjuku Ku, Tokyo 1620826, Japan

来源：

HETEROCYCLES | 2000年 / 52卷 / 02期

关键词：

D O I：

10.3987/COM-99-S84

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of N-formyl-, N-acetyl-, N-ethoxycarbonyl-, and N-methanesulfonyl-1,2,3,4-tetrahydro-6-methoxyisoquinolin-7-ols (1b-e) with lead tetraacetate in dichloromethane (CH2Cl2) produced quantitatively corresponding o-quinol acetates (2b-e), treatment of which with trifluoroacetic acid in CH2Cl2 at 0 degrees C for a few minutes afforded corresponding N-acyl- and N-methanesulfonyl-wilsonirines (4b-e) and N-acyl- and N-methanesulfonylnorsebiferines (5b-e). When the reaction was carried out at room temperature, o-quinol acetates (2d,e) of N-ethoxycarbonyl and N-methanesulfonyl congeners (Id,e) gave 1-[2(ethoxycarbonylamino)ethyl]- and 1-[2-(methanesulfonylamino)ethyl]-4-hydroxy-3,6,7-trimethoxyphenanthrenes (8d,e).

引用

页码：751 / 760

页数：10

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