Selective O-demethylation during bromination of (3,4-dimethoxyphenyl) (2,3,4-trimethoxyphenyl)methanone

被引：15

作者：

Cetinkaya, Yasin ^{[1
]}

Menzek, Abdullah ^{[1
]}

Sahin, Ertan ^{[1
]}

Balaydin, Halis Turker ^{[1
,2
]}

机构：

[1] Ataturk Univ, Dept Chem, Fac Sci, TR-25240 Erzurum, Turkey

[2] Artvin Coruh Univ, Fac Educ, TR-08000 Artvin, Turkey

来源：

TETRAHEDRON | 2011年 / 67卷 / 19期

关键词：

Bromophenol; Bromination; Selective O-demethylation; BROMOPHENOLS; INHIBITION;

D O I：

10.1016/j.tet.2011.03.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(3,4-Dimethoxyphenyl)(2,3,4-trimethoxyphenyl)methanone was synthesized and its bromination was investigated in different conditions. Nine new products (bromophenol derivatives) were isolated in the reactions. These bromophenol derivatives were obtained by selective O-demethylation in its bromination with bromine. The products and their formations were discussed. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3483 / 3489

页数：7

共 24 条

[1] Total Synthesis of the Biologically Active, Naturally Occurring 3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol and Regioselective O-Demethylation of Aryl Methyl Ethers [J].

Akbaba, Yusuf ;

Balaydin, Halis Tuerker ;

Goksu, Sueleyman ;

Sahin, Ertan ;

Menzek, Abdullah .

HELVETICA CHIMICA ACTA, 2010, 93 (06) :1127-1135

[2] First and short syntheses of biologically active, naturally occurring brominated mono- and dibenzyl phenols [J].

Balaydin, Halis T. ;

Akbaba, Yusuf ;

Menzek, Abdullah ;

Sahin, Ertan ;

Goksu, Suleyman .

ARKIVOC, 2009, :75-87

[3] Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product [J].

Balaydin, Halis Turker ;

Gulcin, Ilhami ;

Menzek, Abdullah ;

Goksu, Suleyman ;

Sahin, Ertan .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2010, 25 (05) :685-695

[4] Highly brominated mono- and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity [J].

Duan, Xiao-Juan ;

Li, Xiao-Ming ;

Wang, Bin-Gui .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (07) :1210-1213

[5] 5,7-DICHLORO-3-O-METHYLNORLICHE-XANTHONE, A NEW XANTHONE FROM THE LICHEN LECANORA-BROCCHA [J].

ELIX, JA ;

JIANG, H .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (09) :1591-1595

[6]

FREJKA J, 1936, COLLECT CZECH CHEM C, V8, P130

[7] The natural production of organobromine compounds [J].

Gribble, GJ .

ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH, 2000, 7 (01) :37-49

[8] NATURALLY-OCCURRING ORGANOHALOGEN COMPOUNDS - A SURVEY [J].

GRIBBLE, GW .

JOURNAL OF NATURAL PRODUCTS, 1992, 55 (10) :1353-1395

[9] The diversity of naturally occurring organobromine compounds [J].

Gribble, GW .

CHEMICAL SOCIETY REVIEWS, 1999, 28 (05) :335-346

[10] THE REDUCTION OF BROMO DERIVATIVES OF CATECHOL, RESORCINOL, AND PYROGALLOL [J].

KOHN, M ;

STEINER, L .

JOURNAL OF ORGANIC CHEMISTRY, 1947, 12 (01) :30-33

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