The first Pummerer cyclisations on solid phase. Convenient construction of oxindoles enabled by a sulfur-link to resin

被引：44

作者：

McAllister, LA

Brand, S

de Gentile, R

Procter, DJ

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

[2] Celltech R&D Ltd, Slough SL1 4EN, Berks, England

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 18期

关键词：

D O I：

10.1039/b307586a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-Sulfanyl N-aryl acetamides, attached to resin via the sulfur atom, undergo efficient Pummerer cyclisation upon activation of the sulfur link, to give oxindoles; heterocyclic products can be cleaved from the resin in a traceless manner using samarium(II) iodide.

引用

收藏

页码：2380 / 2381

页数：2

相关论文

共 15 条

[1] Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry [J].

Guillier, F ;

Orain, D ;

Bradley, M .

CHEMICAL REVIEWS, 2000, 100 (06) :2091-2157

[2] A MILD AND CONVENIENT METHOD FOR THE REDUCTION OF ORGANIC HALIDES BY USING A SMI2-THF SOLUTION IN THE PRESENCE OF HEXAMETHYLPHOSPHORIC TRIAMIDE (HMPA) [J].

INANAGA, J ;

ISHIKAWA, M ;

YAMAGUCHI, M .

CHEMISTRY LETTERS, 1987, (07) :1485-1486

[3] Linkers for solid phase organic synthesis [J].

James, IW .

TETRAHEDRON, 1999, 55 (16) :4855-4946

[4] Polymer-supported silyl enol ethers. Synthesis and reactions with imines for the preparation of an amino alcohol library [J].

Kobayashi, S ;

Hachiya, I ;

Suzuki, S ;

Moriwaki, M .

TETRAHEDRON LETTERS, 1996, 37 (16) :2809-2812

[5] Cyclative cleavage via solid-phase supported stabilized sulfur ylides: synthesis of macrocyclic lactones [J].

La Porta, E ;

Piarulli, U ;

Cardullo, F ;

Paio, A ;

Provera, S ;

Seneci, P ;

Gennari, C .

TETRAHEDRON LETTERS, 2002, 43 (05) :761-766

[6] Reduction of α-aryloxy carbonyl compounds with samarium(II) iodide.: A new traceless linker for the solid phase synthesis of carbonyl compounds [J].

McKerlie, F ;

Procter, DJ ;

Wynne, G .

CHEMICAL COMMUNICATIONS, 2002, (06) :584-585

[7] Application of the tandem thionium/N-acyliminium ion cascade toward heterocyclic synthesis [J].

Padwa, A ;

Danca, DM ;

Ginn, JD ;

Lynch, SM .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (05) :571-585

[8]

Padwa A, 1997, SYNTHESIS-STUTTGART, P1353

[9] A selective conversion of sulfide to sulfoxide in hexafluoro-2-propanol [J].

Ravikumar, KS ;

Bégué, JP ;

Bonnet-Delpon, D .

TETRAHEDRON LETTERS, 1998, 39 (20) :3141-3144

[10] Wang p-alkoxyphenylsulfoxide as a new linker and Pummerer cleavage strategy in solid-phase preparation of 1,2-diols [J].

Rolland, C ;

Hanquet, G ;

Ducep, JB ;

Solladié, G .

TETRAHEDRON LETTERS, 2001, 42 (43) :7563-7566