Microwave-assisted sequential amide bond formation and intramolecular amidation: A rapid entry to functionalized oxindoles

被引：80

作者：

Poondra, RR ^{[1
]}

Turner, NJ ^{[1
]}

机构：

[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 05期

关键词：

D O I：

10.1021/ol0473804

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method has been developed for the synthesis of N-substituted oxindoles. The two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide.

引用

页码：863 / 866

页数：4

共 23 条

[1] Enantiodivergent preparation of optically active oxindoles having a stereogenic quaternary carbon center at the C3 position via the lipase-catalyzed desymmetrization protocol: Effective use of 2-furoates for either enzymatic esterification or hydrolysis [J].

Akai, S ;

Tsujino, T ;

Akiyama, E ;

Tanimoto, K ;

Naka, T ;

Kita, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2478-2486

[2] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory studies of intramolecular Heck reactions of (Z)-α,β-unsaturated anilides and mechanistic investigations of asymmetric Heck reactions proceeding via neutral intermediates [J].

Ashimori, A ;

Bachand, B ;

Calter, MA ;

Govek, SP ;

Overman, LE ;

Poon, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6488-6499

[3] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].

Ashimori, A ;

Bachand, B ;

Overman, LE ;

Poon, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487

[4] SYNTHESIS OF OXINDOLES BY RADICAL CYCLIZATION [J].

BOWMAN, WR ;

HEANEY, H ;

JORDAN, BM .

TETRAHEDRON LETTERS, 1988, 29 (50) :6657-6660

[5] LIGAND EFFECTS IN THE RHODIUM(II)-CATALYZED REACTIONS OF ALPHA-DIAZOAMIDES - OXINDOLE FORMATION IS PROMOTED BY THE USE OF RHODIUM(II) PERFLUOROCARBOXAMIDE CATALYSTS [J].

BROWN, DS ;

ELLIOTT, MC ;

MOODY, CJ ;

MOWLEM, TJ ;

MARINO, JP ;

PADWA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2447-2455

[6] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

[7] RHODIUM(II) ACETATE AND NAFION-H CATALYZED DECOMPOSITION OF N-ARYLDIAZOAMIDES - AN EFFICIENT SYNTHESIS OF 2(3H)-INDOLINONES [J].

DOYLE, MP ;

SHANKLIN, MS ;

PHO, HQ ;

MAHAPATRO, SN .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1017-1022

[8] Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C-H functionalization [J].

Hennessy, EJ ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (40) :12084-12085

[9] RHODIUM-CATALYZED CARBONYLATION OF 2-ALKYNYLANILINE - SYNTHESES OF 1,3-DIHYDROINDOL-2-ONES [J].

HIRAO, K ;

MORII, N ;

JOH, T ;

TAKAHASHI, S .

TETRAHEDRON LETTERS, 1995, 36 (35) :6243-6246

[10] CHIRAL INDUCTION IN ARYL RADICAL CYCLIZATIONS [J].

JONES, K ;

MCCARTHY, C .

TETRAHEDRON LETTERS, 1989, 30 (20) :2657-2660

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