Convenient synthesis of 3-alkoxy-3-aryloxindoles by intramolecular arylation of mandelic amides

被引：37

作者：

Hillgren, J. Mikael ^{[1
]}

Marsden, Stephen P. ^{[1
]}

机构：

[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/jo8010842

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Medicinally important 3-alkoxy-3-aryloxindoles are conveniently prepared by the rapid microwave-promoted palladium-catalyzed intramolecular enolate arylation of mandelate-derived anilides.

引用

页码：6459 / 6461

页数：3

共 30 条

[1] Development of an N-heterocyclic carbene ligand based on concept of chiral mimetic [J].

Arao, T ;

Kondo, K ;

Aoyama, T .

TETRAHEDRON LETTERS, 2006, 47 (09) :1417-1420

[2] Asymmetric construction of quaternary carbon stereocenter by Pd-catalyzed intramolecular α-arylation [J].

Arao, Takafumi ;

Kondo, Kazuhiro ;

Aoyama, Toyohiko .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (12) :1743-1747

[3] Simple and convenient synthesis of tertiary benzanilides using dichlorotriphenylphosphorane [J].

Azumaya, I ;

Okamoto, T ;

Imabeppu, F ;

Takayanagi, H .

TETRAHEDRON, 2003, 59 (13) :2325-2331

[4] Highly diastereoselective arylation of (S)-mandelic acid enolate:: Enantioselective synthesis of substituted (R)-3-hydroxy-3-phenyloxindoles and (R)-benzylic acids and synthesis of nitrobenzophenones [J].

Barroso, S ;

Blay, G ;

Cardona, L ;

Fernández, I ;

García, B ;

Pedro, JR .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) :6821-6829

[5] Preparation of 3-spirocyclic indolin-2-ones as ligands for the ORL-1 receptor [J].

Bignan, GC ;

Battista, K ;

Connolly, PJ ;

Orsini, MJ ;

Liu, JC ;

Middleton, SA ;

Reitz, AB .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (22) :5022-5026

[6] ORAL HYPOGLYCEMIC AGENTS - PYRIMIDO[1,2-A]INDOLES AND RELATED-COMPOUNDS [J].

CLIFFE, IA ;

LIEN, EL ;

MANSELL, HL ;

STEINER, KE ;

TODD, RS ;

WHITE, AC ;

BLACK, RM .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (07) :1169-1175

[7] Palladium-catalyzed α-arylation of oxindoles [J].

Durbin, Matthew J. ;

Willis, Michael C. .

ORGANIC LETTERS, 2008, 10 (07) :1413-1415

[8]

Freund R, 2000, HELV CHIM ACTA, V83, P1247, DOI 10.1002/1522-2675(20000607)83:6<1247::AID-HLCA1247>3.0.CO

[9]

2-1

[10] Rhodium-catalyzed addition of aryl boronic acids to 1,2-diketones and 1,2-ketoesters [J].

Ganci, Gregory R. ;

Chisholm, John D. .

TETRAHEDRON LETTERS, 2007, 48 (47) :8266-8269

← 1 2 3 →