A Dramatic Substituent Effect in Silver(I) -Catalyzed Regioselective Cyclization of ortho-Alkynylaryl Aldehyde Oxime Derivatives

被引：93

作者：

Gao, Hongyin ^{[1
]}

Zhang, Junliang ^{[1
,2
]}

机构：

[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 1-2期

基金：

中国国家自然科学基金;

关键词：

alkynes; cyclization; regioselectivity; silver; LEWIS-ACID; ELECTROPHILIC CYCLIZATION; 3,4-DISUBSTITUTED ISOQUINOLINES; O-ALKYNYLBENZALDEHYDES; NUCLEOPHILIC-ADDITION; 4+2 CYCLOADDITION; ALKYNES; BENZANNULATION; ALKENYLATION; 1,2-DIHYDROISOQUINOLINES;

D O I：

10.1002/adsc.200800568

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A dramatic substituent effect was found in the silver(I)-catalyzed cyclization reaction of ortho-alkynylaryl aldehyde oxime derivatives. When R is an alkyl group, the Ag(I)-catalyzed reaction in dimethylacetamide at 110 degrees C (conditions A) affords isoquinolines in good to excellent yields, in contrast, isoquinolin-1(2H)-ones were produced in moderate to high yields under conditions B (dimethylformamide, room temperature) when R is an acetyl group. A plausible mechanism was proposed for this product selectivity control reaction (PSCR) by subtle structure modification.

引用

页码：85 / 88

页数：4

共 55 条

[1] New light-induced iminyl radical cyclization reactions of acyloximes to isoquinolines [J].