Efficient preparation of the isoindoline framework via a six component, tandem double A3-coupling and [2+2+2] cycloaddition reaction

被引：74

作者：

Bonfield, E. Ryan ^{[1
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 03期

关键词：

alkynylation; copper; cycloaddition reaction; domino reaction; multicomponent reaction; rhodium;

D O I：

10.1002/adsc.200700500

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The preparation of tetrasubstituted isoindolines from three alkyne units, two aldehyde units and a primary amine via three consecutive reactions. two aldehyde-amine-alkyne couplings (A(3)-couplings) and a final [2+2+2] cycloaddition, in a single synthetic operation, is described. The A(3)-couplings are catalyzed by copper bromide and the cycloaddition is catalyzed by Wilkinson's catalyst. It was found that many catalysts known to be efficient at the cycloaddition step were not suitable when this step was part of the tandem reaction sequence. Wilkinson's catalyst was found to be unique in its suitability for the overall domino reaction sequence.

引用

页码：370 / 374

页数：5

共 57 条

[1] Scale-up of the green synthesis of azacycloalkanes and isoindolines under microwave irradiation [J].

Barnard, T. Michael ;

Vanier, Grace S. ;

Collins, Michael J., Jr. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (06) :1233-1237

[2] Mild and efficient synthesis of propargylamines by copper-catalyzed Mannich reaction [J].

Bieber, LW ;

da Silva, MF .

TETRAHEDRON LETTERS, 2004, 45 (45) :8281-8283

[3] Efficient ruthenium and copper cocatalzyed five-component coupling to form dipropargyl amines under mild conditions in water [J].

Bonfield, E. Ryan ;

Li, Chao-Jun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (03) :435-437

[4] RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS [J].

BUNCE, RA .

TETRAHEDRON, 1995, 51 (48) :13103-13159

[5] Efficient intermolecular [2+2+2] alkyne cyclotrimerization in aqueous medium using a ruthenium(IV) precatalyst [J].

Cadierno, Victorio ;

Garcia-Garrido, Sergio E. ;

Gimeno, Jose .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) :15094-15095

[6] Benzylic oxidation catalyzed by dirhodium(II,III) caprolactamate [J].

Catino, AJ ;

Nichols, JM ;

Choi, H ;

Gottipamula, S ;

Doyle, MP .

ORGANIC LETTERS, 2005, 7 (23) :5167-5170

[7]

Chessari G., 2006, Preparation of Hydroxybenzamides as Hsp90 Inhibitors, WO, Patent No. [2006109085A1, 2006109085]

[8] [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].

Chopade, Pramod R. ;

Louie, Janis .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327

[9] Synthesis of densely functionalised arenes using [2+2+2] cycloaddition reactions [J].

Clayden, Jonathan ;

Moran, Wesley J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (07) :1028-1030

[10] 5-CHLORO-2-CYCLOHEXYL-L-OXO-6-SULPHAMOYL ISOINDOLINE - NEW DIURETIC [J].

CORNISH, EJ ;

LEE, GE ;

WRAGG, WR .

NATURE, 1963, 197 (487) :1296-&

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