Oxidation with hypervalent iodine reagents .2. Novel cyclohexadienones as precursors for the synthesis of anthraquinones

被引：39

作者：

Mitchell, AS

Russell, RA

机构：

[1] Sch. of Biol. and Chemical Sciences, Deakin University, Waurn Ponds

来源：

TETRAHEDRON | 1997年 / 53卷 / 12期

关键词：

D O I：

10.1016/S0040-4020(97)00110-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidation of substituted phenols with phenyliodonium diacetate in methanol was found to afford 2,4-cyclohexadienones, 2,5-cyclohexadienones or mixtures of isomers, depending on the substrate being oxidized. Annulation of these cyclohexadienones with the anion of 3-cyanophthalide afforded anthraquinones in high yields. (C) 1997 Elsevier Science Ltd.

引用

页码：4387 / 4410

页数：24

共 43 条

[1] ACTION OF ALUMINIUM CHLORIDE ON DERIVATIVES OF ORTHO-BENZOYLBENZOIC ACID
BADDELEY, G
HOLT, G
MAKAR, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1952, (JUN): : 2415 - 2420
[2] Researches on anthraquinones and phthaleins
Bentley, WH
Gardner, HD
Weizmann, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1907, 91 : 1626 - 1640
[3] BIRUKOFF W, 1887, BER DTSCH CHEM GES, V20, P2068
[4] OXIDATION OF SUBSTITUTED HYDROQUINONE MONO-ALKYL ETHERS TO PARA-BENZOQUINONE MONOKETALS
BUCHI, G
CHU, PS
HOPPMANN, A
MAK, CP
PEARCE, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) : 3983 - 3985
[5] The synthesis of phloretin and the preparation of nitrile from phenol-carboxylic acids.
Fischer, E
Nouri, O
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1917, 50 : 611 - 623
[6] MIXED QUINONE MONOKETALS VIA IODOBENZENE DIACETATE OXIDATION
FLECK, AE
HOBART, JA
MORROW, GW
[J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (01) : 179 - 187
[7] REACTIONS OF KETENE ACETALS .15. REGIOSPECIFIC SYNTHESES OF ERYTHROLACCIN AND 7-HYDROXYERYTHROLACCIN
GUAY, V
BRASSARD, P
[J]. TETRAHEDRON, 1984, 40 (24) : 5039 - 5045
[8] HARRIS S. E., 1933, JOUR AMER PHARM ASSOC, V22, P723
[9] ANODIC-OXIDATION OF 4-ALLYL-2-METHOXYPHENOL SYNTHESES OF DEMETHOXYASATONE AND DEMETHOXYISOASATONE
IGUCHI, M
NISHIYAMA, A
TERADA, Y
YAMAMURA, S
[J]. CHEMISTRY LETTERS, 1978, (04) : 451 - 454
[10] IMRE S, 1978, LIEBIGS ANN CHEM, P2018

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