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
ADAM, W
GOLSCH, D
HADJIARAPOGLOU, L
PATONAY, T
[J]. TETRAHEDRON LETTERS, 1991, 32 (08) : 1041 - 1044
[2] DIMETHYLDIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES, ACIDS AND ESTERS
ADAM, W
HADJIARAPOGLOU, L
NESTLER, B
[J]. TETRAHEDRON LETTERS, 1990, 31 (03) : 331 - 334
[3] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS
ADAM, W
CHAN, YY
CREMER, D
GAUSS, J
SCHEUTZOW, D
SCHINDLER, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) : 2800 - 2803
[4] DIMETHYLDIOXIRANE EPOXIDATION OF ENOL PHOSPHATES
ADAM, W
HADJIARAPOGLOU, L
KLICIC, J
[J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6517 - 6520
[5] DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES
ADAM, W
HADJIARAPOGLOU, L
SMERZ, A
[J]. CHEMISCHE BERICHTE, 1991, 124 (01) : 227 - 232
[6] DIMETHYLDIOXIRANE EPOXIDATION OF BETA-OXO ENOL ETHERS
ADAM, W
HADJIARAPOGLOU, L
[J]. CHEMISCHE BERICHTE, 1990, 123 (10) : 2077 - 2079
[7] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS
ADAM, W
CURCI, R
EDWARDS, JO
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) : 205 - 211
[8] EPOXIDATION OF SILYL ENOL ETHERS, PHTHALIDES, AND ENOL ESTERS BY DIMETHYLDIOXIRANE
ADAM, W
HADJIARAPOGLOU, L
WANG, XH
[J]. TETRAHEDRON LETTERS, 1989, 30 (47) : 6497 - 6500
[9] EPOXIDATION OF GAMMA-METHYLENE-GAMMA-BUTYROLACTONES BY DIMETHYLDIOXIRANE
ADAM, W
HADJIARAPOGLOU, L
JAGER, V
SEIDEL, B
[J]. TETRAHEDRON LETTERS, 1989, 30 (32) : 4223 - 4226
[10] ADAM W, IN PRESS CHEM BER

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