Transition-Metal-Free Quinoline Synthesis from Acetophenones and Anthranils via Sequential One-Carbon Homologation/Conjugate Addition/Annulation Cascade

被引：110

作者：

Wakade, Sandip Balasaheb ^{[1
,2
]}

Tiwari, Dipak Kumar ^{[1
,2
]}

Ganesh, Pothapragada S. K. Prabhakar ^{[1
]}

Phanindrudu, Mandalaparthi ^{[1
,2
]}

Likhar, Pravin R. ^{[2
]}

Tiwari, Dharmendra Kumar ^{[1
,2
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Med Chem & Biotechnol Div, Hyderabad 500007, Andhra Pradesh, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110001, India

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 18期

关键词：

SILYL ENOL ETHERS; CATALYZED AEROBIC DEHYDROGENATION; HIGHLY REGIOSELECTIVE SYNTHESIS; DIRECT BETA-ARYLATION; ONE-STEP SYNTHESIS; SUBSTITUTED QUINOLINES; SATURATED KETONES; ORGANIC-SYNTHESIS; TERMINAL ALKYNES; OXIDATIVE CYCLIZATION;

D O I：

10.1021/acs.orglett.7b02429

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition-metal-free method for the construction of functionalized quinolines from readily available acetophenones and anthranils is reported. This one-pot reaction cascade involves in situ generation of alpha,beta-unsaturated ketones from the acetophenone via one-carbon homologation by DMSO followed by the aza-Michael addition of anthranils and subsequent annulation. DMSO acted in this reaction not only as solvent but also as one carbon source, thus providing a highly atom-economical and environmentally benign approach for the synthesis of 3-substituted quinolines.

引用

页码：4948 / 4951

页数：4

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