基于原位捕获胺的Ugi四组分反应及其后修饰串联环化反应:“一锅法”合成六元、七元杂环化合物

doi:10.6023/cjoc202012040

有机化学 ›› 2021, Vol. 41 ›› Issue (6): 2374-2383.DOI: 10.6023/cjoc202012040 上一篇下一篇

研究论文

基于原位捕获胺的Ugi四组分反应及其后修饰串联环化反应:“一锅法”合成六元、七元杂环化合物

刘金妮^a, 谢益碧^a, 阳青青^a, 黄年玉^b, 王龙^a^,^*()

a 三峡大学材料与化工学院无机非金属晶体与能量转换材料重点实验室湖北宜昌 443002
b 三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室湖北宜昌 443002

收稿日期:2020-12-23 修回日期:2021-02-20 发布日期:2021-03-12
通讯作者: 王龙
基金资助:
国家自然科学基金(21602123); 国家自然科学基金(21702001); 高等学校学科创新引智计划(111计划); 高等学校学科创新引智计划(D20015)

Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles

Jinni Liu^a, Yibi Xie^a, Qingqing Yang^a, Nianyu Huang^b, Long Wang^a()

a Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, College of Materials and Chemical Engineering, China Three Gorges University, Yichang, Hubei 443002
b Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Science, China Three Gorges University, Yichang, Hubei 443002

Received:2020-12-23 Revised:2021-02-20 Published:2021-03-12
Contact: Long Wang
Supported by:
National Natural Science Foundation of China(21602123); National Natural Science Foundation of China(21702001); Programme of Introducing Talents of Discipline to Universities (111 Project(D20015)

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摘要/Abstract

报道了一种基于原位捕获胺的Ugi四组分反应及其后修饰串联环化反应策略, 制备了三类六元和七元含氮杂环化合物. 根据该串联反应策略, 胺原位生成, 并立即被捕获参与Ugi四组分反应和随后的修饰串联反应. 从廉价易得的硝基化合物出发, 扩大了底物的适用范围, 并解决了胺易氧化、稳定性和通用性差的问题. 该串联反应策略具有良好的原子经济性和通用性, 是制备含氮杂环化合物的一种新方法. 通过一系列条件控制实验, 提出了反应机理.

关键词: 胺的原位捕获, Ugi四组分反应/Wittig反应, Ugi四组分反应/Staudinger/aza-Wittig反应, 串联反应, 一锅法合成, 杂环化合物

The tandem reaction strategy of Ugi four-component reaction and its subsequent modification reaction based on in situ capture of amines to prepare three types of six- and seven-membered nitrogen-heterocycles are reported. According to this strategy, amines were synthesized in situand immediately worked as the substrate for the Ugi four-component reaction reaction and subsequent modification tandem reaction. Starting from cheap and easily available nitro compounds, the application scope of substrates has been expanded and the problems of amines of easy oxidation, poor stability and versatility have been solved. Furthermore, due to the atom economy and versatility, the tandem reaction strategy has become a new approach for the synthesis of nitrogen-hete- rocycles. In addition, based on a series of conditional control experiments, a plausible mechanism for the reaction is proposed.

Key words: in situcapture of amines, Ugi four-component reaction /Wittig reaction, Ugi four-component reaction/Staudinger/aza-Wittig reaction, tandem reaction, one-pot synthesis, heterocycles

引用此文

刘金妮, 谢益碧, 阳青青, 黄年玉, 王龙. 基于原位捕获胺的Ugi四组分反应及其后修饰串联环化反应:“一锅法”合成六元、七元杂环化合物[J]. 有机化学, 2021, 41(6): 2374-2383.

Jinni Liu, Yibi Xie, Qingqing Yang, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2374-2383.

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图/表 7

图式1. 连续Ugi-4CR/Wittig或aza-Wittig反应制备新型杂环化合物

Scheme 1. Sequential Ugi-4CR/Wittig or aza-Wittig reaction approach to new heterocyclic compounds

Entry	Solvent	Base	T/℃	Yield^b%	Entry	Solvent	Base	T/℃	Yield^b%
1	MeOH	NEt₃	60	N.D.^c	6	Toluene	Na₂CO₃	60	46
2	THF	NEt₃	60	33	7	Toluene	NaOH	60	31
3	DMSO	NEt₃	60	N.D.^c	8	Toluene	DABCO	60	55
4	Toluene	NEt₃	60	79	9	Toluene	NEt₃	30	26
5	Toluene	Cs₂CO₃	60	52	10	Toluene	NEt₃	90	83

表1. 反应条件优化a

Table 1. Optimization of the reaction conditions

表2. 2,3-二氢-1H-2-苯并咪唑啉-1-酮的底物拓展a,b

Table 2. Substrate scope for 2,3-dihydro-1H-2-benzazepin-1-ones

表3. Ugi-4CR/Staudinger/aza-Wittig串联反应制备苯并二氮杂?酮化合物a,b

Table 3. Preparation of benzodiazepines by the Ugi-4CR/Stau- dinger/aza-Wittig tandem reaction

表4. Ugi-4CR/Wittig串联反应制备1,2-二氢异喹啉a,b

Table 4. Preparation of 1,2-dihydroisoquinolines by Ugi-4CR/ Wittig tandem reaction

图式2. 控制实验

Scheme 2. Control experiments

图式3. 可能的反应机理

Scheme 3. Plausible reaction mechanism

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基于原位捕获胺的Ugi四组分反应及其后修饰串联环化反应:“一锅法”合成六元、七元杂环化合物

Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles

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