Regioselective oxidation of 3-monosubstituted juglone derivatives

被引：12

作者：

Couladouros, EA

Strongilos, AT

机构：

[1] Agr Univ Athens, Dept Chem, Athens 11855, Greece

[2] NCSR Demokritos, Organ & Bioorgan Chem Lab, Athens 15310, Greece

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 04期

关键词：

juglone derivatives; oxidation; salcomine; bis(trifluoroacetoxy)iodo]benzene; naphthoquinones;

D O I：

10.1016/S0040-4039(99)02112-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Derivatives of 3-substituted juglones with either electron-withdrawing or -donating substituents are regioselectively oxidized to o- or p-naphthoquinones using salcomine/air or [bis(trifluoroacetoxy)iodo]benzene, respectively. The structure of the oxidation products was confirmed by chemical transformations. A correlation between chemical shift of the single quinoid proton and the quinone structure was established. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：535 / 538

页数：4

相关论文

共 37 条

[1]

BABU B. HARINATH, 1967, PROC INDIAN ACAD SCI SECT A, V66, P301

[2] AN EFFICIENT SYNTHESIS OF JUGLONE [J].

BARRET, R ;

DAUDON, M .

SYNTHETIC COMMUNICATIONS, 1990, 20 (18) :2907-2912

[3] OXIDATION OF PHENOLS TO ORTHO-QUINONES USING DIPHENYLSELENINIC ANHYDRIDE [J].

BARTON, DHR ;

BREWSTER, AG ;

LEY, SV ;

ROSENFELD, MN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (23) :985-986

[4] PREPARATION OF FUNCTIONALIZED JUGLONE ACETATES AND JUGLONES VIA 1,4-DIMETHOXYNAPHTHALENE DERIVATIVES - SYNTHESIS OF ANTHRAQUINONES RELATED TO RHEIN AND ALOE EMODIN [J].

BLOOMER, JL ;

STAGLIANO, KW ;

GAZZILLO, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7906-7912

[5] DIRECTABLE REGIOCHEMISTRY IN NAPHTHAZARINS VIA THE USE OF MASKED DERIVATIVES [J].

BLOOMER, JL ;

STAGLIANO, KW .

TETRAHEDRON LETTERS, 1993, 34 (05) :757-760

[6] TOTAL SYNTHESES OF PHLEICHROME, CALPHOSTIN-A, AND CALPHOSTIN-D - UNUSUAL STEREOSELECTIVE AND STEREOSPECIFIC REACTIONS IN THE SYNTHESIS OF PERYLENEQUINONES [J].

BROKA, CA .

TETRAHEDRON LETTERS, 1991, 32 (07) :859-862

[7] 1,2-dihydro-1,2-dihydroxynaphthalene dehydrogenase containing recombinant strains: Preparation, isolation and characterisation of 1,2-dihydroxynaphthalenes and 1,2-naphthoquinones [J].

Cavallotti, C ;

Orsini, F ;

Sello, G .

TETRAHEDRON, 1999, 55 (14) :4467-4480

[8]

CHEN Z, 1993, LIEBIGS ANN CHEM, P35

[9] ANNELATION REACTIONS OF QUINONE MONOKETALS - STUDIES DIRECTED AT AN EFFICIENT SYNTHESIS OF ANTHRACYCLINONES [J].

CHENARD, BL ;

DOLSON, MG ;

SERCEL, AD ;

SWENTON, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) :318-325

[10] ATROPDIASTEREOSELECTIVE TOTAL SYNTHESIS OF PHLEICHROME AND THE PROTEIN-KINASE-C INHIBITOR CALPHOSTIN-A [J].

COLEMAN, RS ;

GRANT, EB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8795-8796

← 1 2 3 4 →