Synthesis of Furans and Pyrroles from 2-Alkoxy-2,3-dihydrofurans Through a Nucleophilic Substitution-Triggered Heteroaromatization | |
Liu, Changhui1; Zhou, Li1; Huang, Wenbo1; Wang, Man1; Gu YL(顾彦龙)1,2 | |
刊名 | Advanced Synthesis and Catalysis |
2016 | |
卷号 | 358期号:6页码:900-918 |
关键词 | dihydrothiophenes furans heteroaromatization indoles pyrroles alpha-oxoketene dithioacetal |
ISSN号 | 1615-4150 |
通讯作者 | 顾彦龙 |
英文摘要 | An effective method to synthesize -functionalized furan and pyrrole derivatives was developed using 2-alkoxy-2,3-dihydrofurans as modular precursors. This protocol featured a previously unreported tandem nucleophilic substitution/heteroaromatization reaction. Nucleophiles such as indole, -oxoketene dithioacetal, trimethoxybenzene, and dimethoxynaphthalene can react readily with 2-alkoxy-2,3-dihydrofurans to afford -functionalized five-membered ring heterocycles in the presence of acid catalysts, such as copper bromide and iron chloride. The mechanism of the reaction was also discussed, in which the first step, nucleophilic substitution, is the key in triggering the succeeding heteroaromatization. This method can also be extended to the synthesis of dihydrothiophenes. |
学科主题 | 物理化学与绿色催化 |
收录类别 | SCI |
资助信息 | National Natural Science Foundation of China (21173089;21373093);the fundamental research funds for the central universities in China (2014ZZGH019);the Cooperative Innovation Center of Hubei Province |
语种 | 英语 |
WOS记录号 | WOS:000373159200008 |
内容类型 | 期刊论文 |
源URL | [http://210.77.64.217/handle/362003/19984] |
专题 | 兰州化学物理研究所_OSSO国家重点实验室 |
作者单位 | 1.HUST, Sch Chem & Chem Engn, Hubei Key Lab Mat Chem & Serv Failure,Minist Educ, Key Lab Mat Chem Energy Convers & Storage, 1037 Luoyu Rd, Wuhan 430074, Peoples R China 2.Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China |
推荐引用方式 GB/T 7714 | Liu, Changhui,Zhou, Li,Huang, Wenbo,et al. Synthesis of Furans and Pyrroles from 2-Alkoxy-2,3-dihydrofurans Through a Nucleophilic Substitution-Triggered Heteroaromatization[J]. Advanced Synthesis and Catalysis,2016,358(6):900-918. |
APA | Liu, Changhui,Zhou, Li,Huang, Wenbo,Wang, Man,&Gu YL.(2016).Synthesis of Furans and Pyrroles from 2-Alkoxy-2,3-dihydrofurans Through a Nucleophilic Substitution-Triggered Heteroaromatization.Advanced Synthesis and Catalysis,358(6),900-918. |
MLA | Liu, Changhui,et al."Synthesis of Furans and Pyrroles from 2-Alkoxy-2,3-dihydrofurans Through a Nucleophilic Substitution-Triggered Heteroaromatization".Advanced Synthesis and Catalysis 358.6(2016):900-918. |
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