Modular Isoquinoline Synthesis Using Catalytic Enolate Arylation and in Situ Functionalization

被引：48

作者：

Pilgrim, Ben S. ^{[1
]}

Gotland, Alice E. ^{[1
]}

McTernan, Charlie T. ^{[1
]}

Procopiou, Panayiotis A. ^{[2
]}

Donohoe, Timothy J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

H BOND ACTIVATION; ONE-POT SYNTHESIS; ALPHA-ARYLATION; SUBSTITUTED ISOQUINOLINES; EFFICIENT SYNTHESIS; ALKYNES; KETONES; CYCLIZATION; COUPLINGS; PYRIDINES;

D O I：

10.1021/ol4030309

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed alpha-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield.

引用

页码：6190 / 6193

页数：4

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