Substitution and cyclization reactions involving the quasi-antiaromatic 2H-indol-2-one ring system

被引：68

作者：

England, Dylan B. ^{[1
]}

Merey, Gokce ^{[1
]}

Padwa, Albert ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 19期

关键词：

D O I：

10.1021/ol7016438

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The quasi-antiaromatic 2H-indol-2-one ring system is readily generated by treating a 3-hydroxy-substituted 1,3-dihydroindol-2-one with a Lewis acid. Stepwise addition of various pi-nucleophiles to the highly reactive 2H-indol-2-one system occurs smoothly to afford substituted oxindoles. The cyclization was also carried out in an intramolecular fashion to give spiro-substituted oxindoles in good yield.

引用

收藏

页码：3805 / 3807

页数：3

相关论文

共 43 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] Metal-mediated entry to functionalized 3-substituted 3-hydroxyindolin-2-ones via regiocontrolled carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions of isatins in aqueous media [J].

Alcaide, B ;

Almendros, P ;

Rodríguez-Acebes, R .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3198-3204

[3]

[Anonymous], J AM CHEM SOC

[4] 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

[5] SUBSTITUTED OXINDOLES .I. PREPARATION AND SPECTRAL CHARACTERISTICS OF SOME SIMPLE OXINDOLE DERIVATIVES [J].

BECKETT, AH ;

DAISLEY, RW ;

WALKER, J .

TETRAHEDRON, 1968, 24 (19) :6093-&

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

BOWMAN, WR ;

HEANEY, H ;

JORDAN, BM .

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

[7] 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

[8] NONTOXIC LIGANDS IN SAMARIUM DIIODIDE-MEDIATED CYCLIZATIONS [J].

CABRI, W ;

CANDIANI, I ;

COLOMBO, M ;

FRANZOI, L ;

BEDESCHI, A .

TETRAHEDRON LETTERS, 1995, 36 (06) :949-952

[9] A short enantioselective total synthesis of dammarenediol II [J].

Corey, EJ ;

Lin, SZ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (36) :8765-8766

[10] The chemistry of isatins: a review from 1975 to 1999 [J].

da Silva, JFM ;

Garden, SJ ;

Pinto, AC .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (03) :273-324

← 1 2 3 4 5 →