Ugi Four-Component Reaction Based on in-situ Capture of Isocyanide and Post-Modification Tandem Reaction: One-Pot Synthesis of Nitrogen Heterocycles

doi:10.6023/cjoc202108030

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 838-846.DOI: 10.6023/cjoc202108030 Previous Articles Next Articles

ARTICLES

基于原位捕获异腈的Ugi四组分反应及其后修饰串联反应: 一锅法合成含氮杂环化合物

罗享豪^a, 谢益碧^a, 黄年玉^b, 王龙^a^,^c^,^*()

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
c 湖北三峡实验室湖北宜昌 443007

收稿日期:2021-08-18 修回日期:2021-10-08 发布日期:2021-11-09
通讯作者: 王龙
基金资助:
国家自然科学基金(21602123); 高等学校学科创新引智计划(111计划)(D20015)

Ugi Four-Component Reaction Based on in-situ Capture of Isocyanide and Post-Modification Tandem Reaction: One-Pot Synthesis of Nitrogen Heterocycles

Xianghao Luo^a, Yibi Xie^a, Nianyu Huang^b, Long Wang^a^,^c()

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
c China Three Gorges University, Yichang, Hubei 443007

Received:2021-08-18 Revised:2021-10-08 Published:2021-11-09
Contact: Long Wang
Supported by:
National Natural Science Foundation of China(21602123); Program of Introducing Talents of Discipline to Universities (111 Project)(D20015)

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Abstract

A novel strategy of Ugi four-component and post-modification tandem reaction based on in-situ capture of isocyanide is reported in this paper. According to this reaction strategy, the isocyanide was prepared in situ and immediately captured to participate in Ugi four-component reaction and the subsequent modification tandem reaction. Compared with the previous reports, based on in-situ capture of isocyanide was realized in the Ugi four-component reaction and post-modification tandem reaction, which solved the problems of isocyanide instability, high toxicity and unfriendly to the environment in the reaction. Mild reaction system conditions and simplified preparation method provide a novel green and pollution-free strategy for the tandem reaction of Ugi four-component and post modification series reaction with isocyanide.

Key words: in-situ capture of isocyanide, Ugi four-component reaction, post-modification tandem reaction, green isocyanide chemistry, one-pot synthesis

Cite this article

Xianghao Luo, Yibi Xie, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on in-situ Capture of Isocyanide and Post-Modification Tandem Reaction: One-Pot Synthesis of Nitrogen Heterocycles[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 838-846.

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Fig. & Tab. 6

Scheme 1. Reaction strategy of Ugi-4CR/Staudinger/aza-Witting reaction based on in-situ capture of isocyanides

Entry	Solvent	PR₃	Temp./℃	Yield^b/%
1	CH₂Cl₂	PPh₃	r.t.	61
2	CH₂Cl₂	PPh₃	45	84
3	CH₂Cl₂	PPh₃	45	67
4	CH₂Cl₂	PMePh₂	45	63
5	Toluene	PPh₃	45	78
6	THF	PPh₃	45	45
7	CH₃OH	PPh₃	45	29
8	DMSO	PPh₃	45	0

Table 1. Optimization of the reaction conditions

Table 2. Substrate expansion for the synthesis of 5-oxo-4,5- dihydro-3H-benzo[e][1,4]diazepines 5

Table 3. Preparation of 1-oxo-2,3-dihydro-1H-benzo[c]azepine 7 by the Ugi-4CR/Wittig tandem reac-tion

Scheme 2. Condition control experiment

Scheme 3. Proposed possible mechanism

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基于原位捕获异腈的Ugi四组分反应及其后修饰串联反应: 一锅法合成含氮杂环化合物

Ugi Four-Component Reaction Based on in-situ Capture of Isocyanide and Post-Modification Tandem Reaction: One-Pot Synthesis of Nitrogen Heterocycles

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