Synthesis of quinol-4-ones and chroman-4-ones via a palladium-catalysed cascade carbonylation-allene insertion

被引：75

作者：

Grigg, R ^{[1
]}

Liu, A

Shaw, D

Suganthan, S

Woodall, DE

Yoganathan, G

机构：

[1] Univ Leeds, Sch Chem, Mol Innovat Divers & Automated Synth, Leeds LS2 9JT, W Yorkshire, England

[2] Pharmacia & Upjohn Inc, Dept Chem, S-75182 Uppsala, Sweden

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 36期

基金：

英国工程与自然科学研究理事会;

关键词：

palladium catalysis; cascade; carbonylation; allenes; 3-methylene-4-quinolones/chromanones; amino-alcohols;

D O I：

10.1016/S0040-4039(00)01176-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium(0)-catalysed termolecular queuing processes involving oxidative addition to aryl iodides followed by low pressure carbonylation, allene insertion and capture of the resulting pi-allyl palladium(II) species by an internal O- or N-nucleophile occur in good yields. One-pot 3-methylene chromanone/quinolone synthesis-Michael addition-stereoselective reduction are also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7125 / 7128

页数：4

共 9 条

[1] 3 COMPONENT PALLADIUM-CATALYZED CYCLIZATION-CARBONYLATION ANION CAPTURE PROCESSES [J].

GRIGG, R ;

REDPATH, J ;

SRIDHARAN, V ;

WILSON, D .

TETRAHEDRON LETTERS, 1994, 35 (25) :4429-4432

[2] Palladium-catalysed cascade molecular queuing-cycloaddition, cyclocondensation and Diels-Alder reactions [J].

Grigg, R ;

Liu, A ;

Shaw, D ;

Suganthan, S ;

Washington, ML ;

Woodall, DE ;

Yoganathan, G .

TETRAHEDRON LETTERS, 2000, 41 (36) :7129-7133

[3] Palladium catalysed cyclisation-allene insertion-anion capture cascades. [J].

Grigg, R ;

Sridharan, V ;

Terrier, C .

TETRAHEDRON LETTERS, 1996, 37 (24) :4221-4224

[4]

GROHE K, 1992, CHEM BRIT, P34

[5] Structure of a new microbial metabolite, neuchromenin [J].

Hayakawa, Y ;

Yamamoto, H ;

Tsuge, N ;

Seto, H .

TETRAHEDRON LETTERS, 1996, 37 (35) :6363-6364

[6] Palladium-catalyzed carbonylation of o-iodophenols with allenes [J].

Okuro, K ;

Alper, H .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1566-1567

[7]

RISCH N, 1992, LIEBIGS ANN CHEM, P233

[8] ANTI-MICROBIAL 3-METHYLENEFLAVANONES [J].

WARD, FE ;

GARLING, DL ;

BUCKLER, RT ;

LAWLER, DM ;

CUMMINGS, DP .

JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (09) :1073-1077

[9]

WENTLAND MP, 1985, ANNU REP MED CHEM, V20, P145

← 1 →