EPOXIDATION OF FLAVONES BY DIMETHYLDIOXIRANE

被引：51

作者：

ADAM, W ^{[1
]}

GOLSCH, D ^{[1
]}

HADJIARAPOGLOU, L ^{[1
]}

PATONAY, T ^{[1
]}

机构：

[1] LAJOS KOSSUTH UNIV,DEPT ORGAN CHEM,H-4010 DEBRECEN,HUNGARY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 26期

关键词：

D O I：

10.1021/jo00026a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported. These labile epoxides were isolated and completely characterized by UV, IR, H-1 and C-13 NMR, MS, and C, H analyses. Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n. Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f as a mixture of cis and trans isomers.

引用

页码：7292 / 7297

页数：6

共 40 条

[1] DIMETHYLDIOXIRANE EPOXIDATION OF FLAVONES [J].

ADAM, W ;

GOLSCH, D ;

HADJIARAPOGLOU, L ;

PATONAY, T .

TETRAHEDRON LETTERS, 1991, 32 (08) :1041-1044

[2] DIMETHYLDIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES, ACIDS AND ESTERS [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

NESTLER, B .

TETRAHEDRON LETTERS, 1990, 31 (03) :331-334

[3] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].

ADAM, W ;

CHAN, YY ;

CREMER, D ;

GAUSS, J ;

SCHEUTZOW, D ;

SCHINDLER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803

[4] DIMETHYLDIOXIRANE EPOXIDATION OF ENOL PHOSPHATES [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

KLICIC, J .

TETRAHEDRON LETTERS, 1990, 31 (45) :6517-6520

[5] DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

SMERZ, A .

CHEMISCHE BERICHTE, 1991, 124 (01) :227-232

[6] DIMETHYLDIOXIRANE EPOXIDATION OF BETA-OXO ENOL ETHERS [J].

ADAM, W ;

HADJIARAPOGLOU, L .

CHEMISCHE BERICHTE, 1990, 123 (10) :2077-2079

[7] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211

[8] EPOXIDATION OF SILYL ENOL ETHERS, PHTHALIDES, AND ENOL ESTERS BY DIMETHYLDIOXIRANE [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

WANG, XH .

TETRAHEDRON LETTERS, 1989, 30 (47) :6497-6500

[9] EPOXIDATION OF GAMMA-METHYLENE-GAMMA-BUTYROLACTONES BY DIMETHYLDIOXIRANE [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

JAGER, V ;

SEIDEL, B .

TETRAHEDRON LETTERS, 1989, 30 (32) :4223-4226

[10]

ADAM W, IN PRESS CHEM BER

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