Directed ortho metalation cross coupling links.: Carbamoyl rendition of the Baker-Venkataraman rearrangement.: Regiospecific route to substituted 4-hydroxycoumarins

被引：51

作者：

Kalinin, AV

da Silva, AJM

Lopes, CC

Lopes, RSC

Snieckus, V ^{[1
]}

机构：

[1] Univ Waterloo, Guelph Waterloo Ctr Grad Work Chem, Waterloo, ON N2L 3G1, Canada

[2] Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Analit, BR-21949900 Rio De Janeiro, Brazil

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 28期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(98)00977-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a general synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently prepared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence provides a regiospecific anionic Friedel-Crafts complement for the construction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4995 / 4998

页数：4

共 33 条

[1]

BAKER W, 1933, J AM CHEM SOC, V55, P1381

[2]

BARTON DHR, 1992, J CHEM SOC P1, V11, P1365

[3] SYNTHESIS OF BRACHYCOUMARIN AND CYCLOBRACHYCOUMARIN [J].