A new and efficient Baeyer-Villiger rearrangement of flavanone derivatives by the methyltrioxorhenium/H2O2 catalytic system

被引：39

作者：

Bernini, R

Mincione, E

Cortese, M

Aliotta, G

Oliva, A

Saladino, R

机构：

[1] Univ Tuscia, Dipartimento ABAC, I-01100 Viterbo, Italy

[2] Univ Naples Federico II, Dipartimento Sci Vita, I-81100 Caserta, Italy

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 32期

关键词：

Baeyer-Villiger reactions; lactonisation; flavanones; flavonoids;

D O I：

10.1016/S0040-4039(01)01005-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic Baeyer-Villiger rearrangement of flavanones is described by the use of the homogeneous methyltrioxorhenium (MTO)/H2O2 system. In these experimental conditions 3,4-dihydro-4-phenyl-1,5-benzodioxepin-2-ones and previously not reported para-quinone derivatives have been obtained in mild experimental conditions from acceptable to good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5401 / 5404

页数：4

相关论文

共 29 条

[1] OXIDATION OF METHOXYBENZENES TO P-BENZOQUINONES CATALYZED BY METHYLTRIOXORHENIUM(VII) [J].

ADAM, W ;

HERRMANN, WA ;

SAHAMOLLER, CR ;

SHIMIZU, M .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 97 (01) :15-20

[2] Kinetics and mechanism of the epoxidation of alkyl-substituted alkenes by hydrogen peroxide, catalyzed by methylrhenium trioxide [J].

AlAjlouni, AM ;

Espenson, JH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12) :3969-3976

[3] An efficient oxyfunctionalisation by dimethyldioxirane of the benzylethereal carbon of flavonoids; A general and useful way to anthocyanidins [J].

Bernini, R ;

Mincione, E ;

Sanetti, A ;

Bovicelli, P ;

Lupattelli, P .

TETRAHEDRON LETTERS, 1997, 38 (26) :4651-4654

[4] Influence of tangeretin on tamoxifen's therapeutic benefit in mammary cancer [J].

Bracke, ME ;

Depypere, HT ;

Boterberg, T ;

Van Marck, VL ;

Vennekens, KM ;

Vanluchene, E ;

Nuytinck, M ;

Serreyn, R ;

Mareel, MM .

JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1999, 91 (04) :354-359

[5] Investigating the mode of action of natural phytotoxins [J].

Dayan, FE ;

Romagni, JG ;

Duke, SO .

JOURNAL OF CHEMICAL ECOLOGY, 2000, 26 (09) :2079-2094

[6]

Galati EM, 1996, FARMACO, V51, P219

[7] SYNTHESIS AND STRUCTURE OF 3,4-DIHYDRO-4-PHENYL-1,5-BENZODIOXEPIN-2-ONES [J].

GELEBE, AC ;

KAYE, PT ;

LIDDELL, JR .

SYNTHETIC COMMUNICATIONS, 1991, 21 (22) :2263-2268

[8]

HERMANN WA, 1991, ANGEW CHEM, V103, P1706

[9] MULTIPLE BONDS BETWEEN MAIN-GROUP ELEMENTS AND TRANSITION-METALS .133. METHYLTRIOXORHENIUM AS A CATALYST OF THE BAEYER-VILLIGER OXIDATION [J].

HERRMANN, WA ;

FISCHER, RW ;

CORREIA, JDG .

JOURNAL OF MOLECULAR CATALYSIS, 1994, 94 (02) :213-223

[10] MULTIPLE BONDS BETWEEN MAIN-GROUP ELEMENTS AND TRANSITION-METALS .125. ALKYLRHENIUM OXIDES AS HOMOGENEOUS EPOXIDATION CATALYSTS - ACTIVITY, SELECTIVITY, STABILITY, DEACTIVATION [J].

HERRMANN, WA ;

FISCHER, RW ;

RAUCH, MU ;

SCHERER, W .

JOURNAL OF MOLECULAR CATALYSIS, 1994, 86 (1-3) :243-266