Synthesis of Quinolines via Iron-Catalyzed Redox Condensation of Alcohols with 2-Nitrobenzyl Methyl Ether/2-Nitrobenzyl Alcohols

Qi Wang; Meirong Wang; Hui-Jing Li; Shuai Zhu; Ying Liu; Yan-Chao Wu

doi:10.1055/s-0035-1562496

Synthesis, Table of Contents

Synthesis 2016; 48(22): 3985-3995
DOI: 10.1055/s-0035-1562496

paper

Synthesis of Quinolines via Iron-Catalyzed Redox Condensation of Alcohols with 2-Nitrobenzyl Methyl Ether/2-Nitrobenzyl Alcohols

Qi Wang

^aSchool of Marine Science and Technology, Harbin Institute of Technology, No. 2 Wenhuaxi Road, Weihai 264209, P. R. of China Email: liuying@iccas.ac.cn Email: ycwu@iccas.ac.cn

,

Meirong Wang

^bSchool of Materials Science and Engineering, Harbin Institute of Technology, No. 2 Wenhuaxi Road, Weihai 264209, P. R. of China

,

Hui-Jing Li

^aSchool of Marine Science and Technology, Harbin Institute of Technology, No. 2 Wenhuaxi Road, Weihai 264209, P. R. of China Email: liuying@iccas.ac.cn Email: ycwu@iccas.ac.cn

,

Shuai Zhu

^aSchool of Marine Science and Technology, Harbin Institute of Technology, No. 2 Wenhuaxi Road, Weihai 264209, P. R. of China Email: liuying@iccas.ac.cn Email: ycwu@iccas.ac.cn

,

Ying Liu*

^aSchool of Marine Science and Technology, Harbin Institute of Technology, No. 2 Wenhuaxi Road, Weihai 264209, P. R. of China Email: liuying@iccas.ac.cn Email: ycwu@iccas.ac.cn

,

Yan-Chao Wu*

^aSchool of Marine Science and Technology, Harbin Institute of Technology, No. 2 Wenhuaxi Road, Weihai 264209, P. R. of China Email: liuying@iccas.ac.cn Email: ycwu@iccas.ac.cn

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Abstract

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Abstract

An iron-catalyzed redox condensation of 2-nitrobenzyl alcohols, formic acid, and alcohols has been developed, which affords substituted quinolines with carbon dioxide and water as the only side products. With the use of formic acid as a redox moderator to fill the electron gap of the global redox condensation process, the reaction goes smoothly with a smaller amount of alcohol in comparison to previous reports (i.e. 1.2 equiv versus 3.3–4 equiv). The reaction goes equally well when 2-nitrobenzyl methyl ether was used instead of 2-nitrobenzyl alcohol under otherwise identical conditions, shedding a new light on the study of this quinoline synthetic method.

Key words

quinolines - 2-nitrobenzyl alcohols - iron catalysis - redox condensation - Friedländer annulation

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