A biomimetic oxidizing system ''Cu2+-ascorbic acid-O-2'': Its distinctive hydroxylation activity of aromatic compounds, reaction mechanism, and application to the synthesis of new bioactive molecules

被引：1

作者：

Aihara, K

Urano, Y

Higuchi, T

Hirobe, M

机构：

[1] Faculty of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 1997年 / 55卷 / 03期

关键词：

D O I：

10.5059/yukigoseikyokaishi.55.196

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A biomimetic oxidizing system ''Cu2+-ascorbic acid-O-2'' was effective for selective conversion of o-alkoxyphenols into oxido-labile catechols. First direct preparation of 3-hydroxycoumarins from coumarins was achieved by using this system. The oxidizing system hydroxylated phenols to afford catechols and hydroquinones. An unusual substituent effect was observed on this hydroxylation of phenols. Some of the derived catechols and 3-hydroxycoumarins exhibited much greater bio-activities than those of the mother compounds. Mechanistic investigation has revealed that catechols were formed via ipso-substitution of alkoxy groups of o-alkoxyphenols for hydroxy group.

引用

页码：196 / 206

页数：11

共 39 条

[1]

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[2]

AIHARA K, 1988, CHEM PHARM BULL, V36, P837

[3]

AIHARA K, 1990, CHEM PHARM BULL, V38, P842

[4] 3-HYDROXYCOUMARINS - 1ST DIRECT PREPARATION FROM COUMARINS USING A CU-2+ ASCORBIC-ACID O2 SYSTEM, AND THEIR POTENT BIOACTIVITIES [J].