SYNTHESES IN ISOQUINOLINE SERIES . SELECTIVE DEMETHYLATION OF 6,7- AND 7,8-DIMETHOXY-2,3-DIHYDRO-4(1H)-ISOQUINOLONES

被引：23

作者：

GRETHE, G

TOOME, V

LEE, HL

USKOKOVI.M

BROSSI, A

机构：

[1] Chemical Research Department, Hoffmann-La Roche, Inc., Nutley

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1968年 / 33卷 / 02期

关键词：

D O I：

10.1021/jo01266a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 6,7- and 7,8-dimethoxy-2,3-dihydro-4(1H)-isoquinolones with a 1:1 mixture of 48% aqueous hydrobromic acid and glacial acetic acid at 115° leads to selective ether cleavage of the methoxyl group in position 6 or 8, respectively. The structure of the reaction products was ascertained by chemical transformation to the corresponding 1,2,3,4-tetrahydroisoquinolines and by ultraviolet analysis. This selective demethylation provides an easy route to 6-hydroxy-7-methoxy- or 8-hydroxy-7-methoxyisoquinoline derivatives. © 1968, American Chemical Society. All rights reserved.

引用

页码：504 / &

共 13 条

[1]

BEKE D, 1958, ACTA CHIM HUNG, V14, P325

[2] SYNTHESIS OF ISOQUINOLINES .3. A NEW SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES [J].