Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction:

doi:10.6023/cjoc202012040

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2374-2383.DOI: 10.6023/cjoc202012040 Previous Articles Next Articles

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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

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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Abstract

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

Cite this article

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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Fig. & Tab. 7

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

Table 1. Optimization of the reaction conditions

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

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

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

Scheme 2. Control experiments

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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