Trifluoroacetic Acid Mediated One-Pot Synthesis of Furo-Fused Quinoxalines/Pyrazines

被引：18

作者：

Saini, Kapil Mohan ^{[1
]}

Kumar, Sonu ^{[1
]}

Patel, Monika ^{[1
]}

Saunthwal, Rakesh K. ^{[1
]}

Verma, Akhilesh K. ^{[1
]}

机构：

[1] Univ Delhi, Dept Chem, Delhi 110007, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 25期

关键词：

Nitrogen heterocycles; Cyclization; Cross-coupling; Alkynes; Oxygen heterocycles; Fused-ring systems; CATALYZED DOMINO REACTIONS; C-H ACTIVATION; ELECTROPHILIC CYCLIZATION; BIOLOGICAL-ACTIVITY; CASCADE REACTION; PALLADIUM; ALKYNES; HETEROCYCLES; STRATEGY; ANALOGS;

D O I：

10.1002/ejoc.201700541

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A trifluoroacetic acid promoted step-economical one-pot approach to the synthesis of furo-fused quinoxalines/pyrazines by the reaction of 2,3-dichloroquinoxalines/pyrazines with alkynes is described. The reaction involves a selective insitu Sonogashira coupling step and a hydroxylation followed by a metal-free 5-endo-dig cyclization. Preliminary experiments show that trifluoroacetic acid acts as a source of oxygen for the oxyarylation step, and isotopic labeling studies support the proposal that the mechanistic pathway involves activation of the alkyne by the acidic medium. Various kinds of substituents are tolerated, which should prove valuable for structural and biological investigations.

引用

页码：3707 / 3715

页数：9

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