Base-catalyzed condensation of 2-hydroxybenzaldehydes with α,β-unsaturated aldehydes -: Scope and limitations

被引：70

作者：

Lesch, B

Toräng, J

Vanderheiden, S

Bräse, S

机构：

[1] Univ Karlsruhe, Inst Organ Chem, TH, D-76131 Karlsruhe, Germany

[2] Univ Bonn, Inst Organ Chem, D-53121 Bonn, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 04期

关键词：

gamma-aldol reaction; enols; enones; nucleophilic addition; oxygen heterocycles;

D O I：

10.1002/adsc.200404239

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The base-catalyzed condensation of alpha,beta-unsaturated carbonyl compounds with 2-hydroxybenzaldehydes yielding tetrahydroxanthones and dihydrobenzopyrans has been investigated. A novel access to highly functionalized dihydrobenzopyrans via a mild generation of the dienol of senecialdehyde and subsequent conjugated aldol reaction has been reported.

引用

页码：555 / 562

页数：8

共 39 条

[1] First-examples of metal and ligand accelerated catalysis of the Baylis-Hillman reaction [J].

Aggarwal, VK ;

Tarver, GJ ;

McCague, R .

CHEMICAL COMMUNICATIONS, 1996, (24) :2713-2714

[2] THE COMPLEX FORMATION BETWEEN IRON(III)ION AND SOME PHENOLS .4. THE ACIDITY CONSTANT OF THE PHENOLIC GROUP [J].

AGREN, A .

ACTA CHEMICA SCANDINAVICA, 1955, 9 (01) :49-56

[3] NOVEL METHODS FOR SYNTHESIS OF 2-2-DIMETHYLCHROMENS [J].

BANDARANAYAKE, WM ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (17) :970-+

[4] 3-HYDROXY-3-METHYL-1,1-DIMETHOXYBUTANE, A NEW REAGENT FOR DIMETHYL-CHROMENYLATION - SYNTHESIS OF LONCHOCARPIN, JACAREUBIN, EVODIONOL METHYL ETHER, AND OTHER CHROMENS [J].

BANDARANAYAKE, WM ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (04) :811-+

[5]

Baylis A. B, 1972, German Patent, Patent No. 2155113

[6] ANTIINFLAMMATORY MECHANISM OF CORDIACHROMENE-A ACTION [J].

BENSLIMANE, AF ;

POUCHUS, YF ;

VERBIST, JF ;

PETIT, JY ;

BRION, JD ;

WELIN, L .

JOURNAL OF CLINICAL PHARMACOLOGY, 1995, 35 (03) :298-301

[7]

Bouzbouz S, 2000, EUR J ORG CHEM, V2000, P3223

[8] SYNTHESIS OF UNSATURATED 5-HYDROXY-ACIDS AND 7-OXO-ACIDS BY ADDITION OF UNSATURATED CARBOXYLIC-ACID DIENOLATES TO CARBONYL-COMPOUNDS [J].

CASINOS, I ;

MESTRES, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (12) :1651-1655

[9]

Claisen L., 1914, LIEBIGS ANN CHEM, V401, P21

[10] CONVERSION OF PHENOLS INTO CHROMENS - REGIOSPECIFICITY AND SCOPE [J].

CLARKE, DG ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (09) :1007-1015

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