Metal-Free, Ionic Liquid-Mediated Synthesis of Functionalized Quinolines

被引：41

作者：

Bharate, Jaideep B. ^{[1
,2
]}

Bharate, Sandip B. ^{[1
,2
]}

Vishwakarma, Ram A. ^{[1
,2
]}

机构：

[1] CSIR, Indian Inst Integrat Med, Med Chem Div, Jammu 180001, India

[2] CSIR, Indian Inst Integrat Med, Acad Sci & Innovat Res AcSIR, Jammu 180001, India

来源：

ACS COMBINATORIAL SCIENCE | 2014年 / 16卷 / 11期

关键词：

ionic liquids; metal-free; quinolines; heterocycle synthesis; green chemistry; SOLVENT-FREE CONDITIONS; POLYSUBSTITUTED QUINOLINES; COUPLING REACTIONS; SALTS; MECHANISM; CLEAVAGE; PROTOCOL; COMPLEX; ALKENES; ALKYNES;

D O I：

10.1021/co500047w

中图分类号：

O69 [应用化学];

学科分类号：

070301 [无机化学];

摘要：

An expedient and metal-free synthetic protocol for construction of substituted quinolines has been developed from anilines and phenylacetaldehydes using imidazolium cation-based ionic liquids as the reaction medium. Mechanistic analysis indicated that the reaction occurs through C-C and C-N bond formation to produce isolable 2,3-disubstituted quinoline intermediates, which undergo C-C bond cleavage to produce 3-substituted quinolines. The reaction proceeds smoothly with a range of functionalities in good to excellent yields. Advantages of this protocol include metal-free, environmentally friendly, recyclable reaction media, higher yields and shorter reaction times, and thus is promising for the efficient combinatorial synthesis of structurally diverse 2,3-disubstituted and 3-substituted quinolines.

引用

页码：624 / 630

页数：7

共 39 条

[1]

Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines [J].