Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines

doi:10.6023/cjoc202401034

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2286-2295.DOI: 10.6023/cjoc202401034 Previous Articles Next Articles

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可见光促进活化烯烃叠氮化/环化反应合成吲哚[2,1-a]异喹啉酮衍生物研究

唐裕才^*(), 何宇鹏, 杨碧玉, 段京林, 杜昌远, 蒋洁, 李佳丽, 潘若涵, 陈宇, 刘学文

湖南文理学院化学与材料工程学院水处理功能材料湖南省重点实验室电镀废水回用技术湖南省工程技术研究中心湖南常德 415000

收稿日期:2024-01-29 修回日期:2024-03-19 发布日期:2024-04-10
基金资助:
湖南省教育厅科学研究基金(23B0650); 湖南省自然科学基金(2022JJ30418); 湖南文理学院重点研究项目(22ZD04); 大学生创新创业训练(XDC202318)

Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines

Yucai Tang(), Yupeng He, Biyu Yang, Jinglin Duan, Changyuan Du, Jie Jiang, Jiali Li, Ruohan Pan, Yu Chen, Xuewen Liu

Hunan Provincial Key Laboratory of Water Treatment Functional Materials, Hunan Province Engineering Research Center of Electroplating Wastewater Reuse Technology, College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde, Hunan 415000

Received:2024-01-29 Revised:2024-03-19 Published:2024-04-10
Contact: * E-mail: yctang1009@163.com
Supported by:
Scientific Research Foundation of Hunan Provincial Education Department(23B0650); Natural Science Foundation of Hunan Province(2022JJ30418); Key Scientific Research Foundation of Hunan University of Arts and Science(22ZD04); Innovation and Entrepreneurship Training Program for College Students of Hunan University of Arts and Science(XDC202318)

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Abstract

An efficient visible-light-induced radical cascade azidation/cyclization of 2-aryl indoles with trimethylsilyl azide (TMSN₃) has been developed using organic dye Rose Bengal as the photocatalyst. This method did not require metal catalysts and additives, and used air as the oxidant to obtain diverse indolo[2,1-a]isoquinolin-6(5H)-ones in moderate to good yields. Mechanistic studies demonstrated that the reaction proceeded via a radical pathway.

Key words: Rose Bengal, visible-light, 2-aryl indole, azidation, indolo[2,1-a]isoquinolin-6(5H)-one

Cite this article

Yucai Tang, Yupeng He, Biyu Yang, Jinglin Duan, Changyuan Du, Jie Jiang, Jiali Li, Ruohan Pan, Yu Chen, Xuewen Liu. Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2286-2295.

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Fig. & Tab. 7

Scheme 1. Strategies for the synthesis of azide compounds

Entry	Organic dye	Solvent	Yield^b/%
1	Eosin B	DCE	18
2	Fluorescein	DCE	8
3	Rose Bengal	DCE	31
4	Na₂-EosinY	DCE	30
5	Ru(bpy)₃Cl₂•6H₂O	DCE	0
6^c	Rose Bengal	DCE	35
7^d	Rose Bengal	DCE	28
8^c	Rose Bengal	CH₂Cl₂	50
9^c	Rose Bengal	CH₃CN	45
10^c	Rose Bengal	THF	22
11^c	Rose Bengal	DMSO	87
12^c	Rose Bengal	DMF	39
13^c	Rose Bengal	1,4-Dioxane	57
14^c	Rose Bengal	CH₃OH	0
15^c^,^e	Rose Bengal	DMSO	26
16^c	—	DMSO	0
17^c^,^f	Rose Bengal	DMSO	0

Table 1. Optimization of reaction conditionsa

Table 2. Substrate scope for the synthesis of azidated indolo[2,1-a]isoquinolinesa

Scheme 2. Synthetic utility of methodology

Scheme 3. Radical trapping experiments with TEMPO and BHT

Figure 1. (a) Fluorescence response of 5 mmol/L photocatalyst Rose Bengal to TMSN3 in DMSO solution and (b) linear curve between fluorescent emission ratio (I0/I) of Rose Bengal and the concentrations of TMSN3

Scheme 4. Proposed reaction mechanism

References 18

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可见光促进活化烯烃叠氮化/环化反应合成吲哚[2,1-a]异喹啉酮衍生物研究

Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines

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Fig. & Tab. 7

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