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

doi:10.6023/cjoc202401034

有机化学 ›› 2024, Vol. 44 ›› Issue (7): 2286-2295.DOI: 10.6023/cjoc202401034 上一篇下一篇

研究论文

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)

文章分享

1. 242286S.pdf(4167KB)

摘要/Abstract

发展了一种以Rose Bengal为有机染料光催化剂, 在可见光照射下实现2-芳基吲哚与叠氮三甲基硅烷(TMSN₃)的自由基叠氮化/环化反应构建叠氮基取代吲哚[2,1-a]异喹啉酮衍生物的方法. 该方法无需金属催化剂和添加剂, 以空气为氧化剂, 以中等到良好的收率得到结构多样的吲哚[2,1-a]异喹啉酮类化合物. 机理验证实验表明, 该反应经历了自由基历程.

关键词: Rose Bengal, 可见光, 2-芳基吲哚, 叠氮化, 吲哚[2,1-a]异喹啉酮

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

引用此文

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. 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[J]. 有机化学, 2024, 44(7): 2286-2295.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 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

参考文献 18

[1]	(a) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188. pmid: 23531040
	(b) Bräse, S.; Banert, K. Organic Azides: Syntheses and Applications, Wiley, New York, 2010. pmid: 23531040
	(c) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905. doi: 10.1021/cr200409f pmid: 23531040
[2]	Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297.
[3]	Kumar, R.; Wang, L. L.; Wiebe, L. I.; Knaus, E. E. J. Med. Chem. 1994, 37, 4297. pmid: 7996541
[4]	(a) Borreguero, A. M.; Muñoz, M.; Haro, J. C. D.; Carmona, M.; Rodríguez, J. F. React. Funct. Polym. 2016, 101, 1.
	(b) Vora, A.; Nasrullah, M. J.; Webster, D. C. J. Coat. Technol. Res. 2010, 7, 409.
[5]	(a) Patai, S. The Chemistry of the Azido Group, Wiley, London, 1971. pmid: 23980438
	(b) Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278. pmid: 23980438
	(c) Tanimoto, H.; Kakiuchi, K. Nat. Prod. Commun. 2013, 8, 1021. pmid: 23980438
	(d) Lahabb, J. Click Chemistry for Biotechnology and Materials Science, Wiley, London, 2009. pmid: 23980438
	(e) Gao, Y.; Zhang, X.; Yu, J.; Zhou, J. Acta Chim. Sinica 2023, 81, 1590. (in Chinese) pmid: 23980438
	(高杨, 张学鑫, 余金生, 周剑, 化学学报, 2023, 81, 159.) pmid: 23980438
[6]	Sivaguru, P.; Ning, Y.; Bi, X. Chem. Rev. 2021, 121, 4253.
[7]	Matcha, K.; Narayan, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2013, 52, 7985. doi: 10.1002/anie.201303550 pmid: 23788465
[8]	Wang, J.-J.; Yu, W. Chem.-Eur. J. 2019, 25, 3510.
[9]	Ge, L.; Zhou, H.; Chiou, M.-F.; Jiang, H.; Jian, W.; Ye, C.; Li, X.; Zhu, X.; Xiong, H.; Li, Y.; Song, L.; Zhang, X.; Bao, H. Nat. Catal. 2021, 4, 28.
[10]	(a) Xie, J.; Jin, H.; Xu, P.; Zhu, C. Tetrahedron Lett. 2014, 55, 36.
	(b) Reckenthälera, M.; Griesbeck, A. G. Adv. Synth. Catal. 2013, 355, 2727.
	(c) Xuan, J.; Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Eur. J. Org. Chem. 2013, 2013, 6755.
	(d) Zou, Y.-Q.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2013, 52, 11701.
	(e) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
	(f) Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387.
	(g) Shang, T.-Y.; Lu, L.-H.; Cao, Z.; Liu, Y.; He, W.-M.; Yu, B. Chem. Commun. 2019, 55, 5408.
	(h) Chen, J.-Y.; Wu, H.-Y.; Song, H.-Y.; Li, H.-X.; Yang, T.-B.; He, W.-M. J. Org. Chem. 2023, 88, 8360.
	(i) Song, H.-Y.; Xiao, F.; Jiang, J.; Wu, C.; Ji, H.-T.; Lu, Y.-H.; Wang, K.-L.; He, W.-M. Chin. Chem. Lett. 2023, 34, 108509.
	(j) Sun, Y-L.; Tan, F.-F.; Hu R.-G.; Hu C.-H.; Li Y. Chin. J. Chem., 2022, 40, 1903.
[11]	For recent examples using organic dyes as the photoredox catalyst see: (a) Rueping, M.; Vila, C.; Bootwicha, T. ACS Catal. 2013, 3, 1676. pmid: 23101908
	(b) Hari, D. P.; Schroll, P.; König, B. J. Am. Chem. Soc. 2012, 134, 2958. pmid: 23101908
	(c) Hari, D. P.; Hering, T.; König, B. Org. Lett. 2012, 14, 5334. pmid: 23101908
	(d) Hering, T.; Hari, D. P.; König, B. J. Org. Chem. 2012, 77, 10347. doi: 10.1021/jo301984p pmid: 23101908
	(e) Liu, Q.; Li, Y.-N.; Zhang, H.-H.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Chem.-Eur. J. 2012, 18, 620. pmid: 23101908
	(f) Fidaly, K.; Ceballos, C.; Falguières, A.; Veitia, M. S.-I.; Guy, A.; Ferroud, C. Green Chem. 2012, 14, 1293. pmid: 23101908
[12]	Zhou, N.; Xia, Z.; Wu, S.; Kuang, K.; Xu, Q.; Zhang, M. J. Org. Chem. 2021, 86, 15253.
[13]	Kulthe, A. D.; Jaiswal, S.; Golagani, D.; Mainkar, P. S.; Akondi, S. M. Org. Biomol. Chem. 2022, 20, 4534.
[14]	(a) Wei, W.; Cui, H. H.; Yue, H. L.; Yang, D. S. Green Chem. 2018, 20, 3197.
	(b) Pei, C.; Liu, Y.; Chen, X.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Adv. Synth. Catal. 2023, 356, 860.
	(c) Wu, X.; Zhang, X.; Ji, X.; Deng, G.-J.; Huang, H. Org. Lett. 2023, 25, 5162.
[15]	(a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev, 2003, 103, 893. pmid: 20380420
	(b) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489. doi: 10.1021/cr900211p pmid: 20380420
	(c) Somei, M.; Yamada, F. Nat. Prod. Rep. 2004, 21, 278. pmid: 20380420
[16]	(a) Li, H.-C.; Sun, K.; Li, X.; Wang, S.-Y.; Chen, X.-L.; He, S.-Q.; Qu, L.-B.; Yu, B. J. Org. Chem. 2021, 86, 9055. pmid: 34812822
	(b) Pan, Y.; Gong, X.; Hao, R.; Zeng, S.; Xu, J.; Shen, Z.; Huang, W. Asian J. Org. Chem. 2022, 11, e202100766. pmid: 34812822
	(c) Hu, X.-Y.; Xu, H.-F.; Chen, Q.; Pan, Y.-L.; Chen, J.-Z. Org. Biomol. Chem. 2021, 19, 10376. doi: 10.1039/d1ob01917a pmid: 34812822
	(d) Wei, Y.-L.; Chen, J.-Q.; Sun, B.; Xu, P.-F. Chem. Commun. 2019, 55, 5922. pmid: 34812822
	(e) Cui, H.; Ni, C.; Zhang, C. J. Org. Chem., 2021, 86, 15835. pmid: 34812822
	(f) Luo, Y.; Tian, T.; Nishihara, Y.; Lv, L.; Li, Z. Chem. Commun. 2021, 57, 9276. pmid: 34812822
	(g) Zhang, J.-R.; Liu, H.-Y.; Fan, T.; Chen, Y.-Y.; Xu, Y.-L. Adv. Synth. Catal. 2021, 363, 497. pmid: 34812822
[17]	(a) Maiti, D.; Mahanty, K.; Sarkar, S. D. Chem.-Asian J. 2021, 16, 748. pmid: 35515398
	(b) Srivastava, A.; Singh, P. K.; Ali, A.; Singh, P. P.; Srivastava, V. RSC Adv. 2020, 10, 39495. doi: 10.1039/d0ra07400d pmid: 35515398
[18]	Chen, Y.-X.; Wang, Z.-J.; Xiao, J.-A.; Chen, K.; Xiang, H.-Y.; Yang, H. Org. Lett. 2021, 23, 6558.

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

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 7

参考文献 18

相关文章 15

编辑推荐

相关统计

本文评价

[1]	傅艳华, 徐畅, 张超, 王怡莎, 冯高峰. 可见光诱导铁催化氮杂环的羟甲基化[J]. 有机化学, 2024, 44(7): 2265-2273.
[2]	段东森, 马媛, 刘宇博, 程富, 朱道勇, 王少华. 可见光诱导的二氧化碳对活化烯烃的脱碳羧基化反应[J]. 有机化学, 2024, 44(5): 1675-1685.
[3]	曹香雪, 贾雅会, 殷世纪, 徐亮, 韦玉, 宋欢欢. 可见光诱导二氢喹唑啉酮碳碳键断裂与三氟甲基取代烯烃的脱氟烷基化反应研究[J]. 有机化学, 2024, 44(5): 1549-1557.
[4]	陈雯雯, 张琴, 张松月, 黄芳芳, 张馨尹, 贾建峰. 无光催化剂条件下可见光诱导炔基碘和亚磺酸钠偶联反应[J]. 有机化学, 2024, 44(2): 584-592.
[5]	朱彦硕, 王红言, 舒朋华, 张克娜, 王琪琳. 烷氧自由基引发1,5-氢原子转移实现C(sp³)—H键官能团化的研究进展[J]. 有机化学, 2024, 44(1): 1-17.
[6]	童红恩, 郭宏宇, 周荣. 可见光促进惰性碳-氢键对羰基的加成反应进展[J]. 有机化学, 2024, 44(1): 54-69.
[7]	徐伟, 翟宏斌, 程斌, 汪太民. 可见光诱导的钯催化Heck反应[J]. 有机化学, 2023, 43(9): 3035-3054.
[8]	樊思捷, 董武恒, 梁彩云, 王贵超, 袁瑶, 尹作栋, 张兆国. 可见光诱导的自由基环化反应构建4-芳基-1,2-二氢萘类化合物[J]. 有机化学, 2023, 43(9): 3277-3286.
[9]	杨晓娜, 郭宏宇, 周荣. 可见光促进有机硅化合物参与的化学转化[J]. 有机化学, 2023, 43(8): 2720-2742.
[10]	高艳华, 张银潘, 张妍, 宋涛, 杨勇. 可见光驱动表面富含氧空位Nb₂O₅催化醇氧化反应[J]. 有机化学, 2023, 43(7): 2572-2579.
[11]	吴敏, 刘博, 袁佳龙, 付强, 汪锐, 娄大伟, 梁福顺. 可见光媒介的C—S键构建反应研究进展[J]. 有机化学, 2023, 43(7): 2269-2292.
[12]	刘静, 郝健, 沈其龙. 可见光促进的含色氨酸寡肽与YlideFluor试剂的直接三氟甲基化反应研究[J]. 有机化学, 2023, 43(4): 1517-1524.
[13]	魏芳, 余鑫, 肖强. 有机叠氮化合物参与的反应: C—N₃基团保留的研究进展[J]. 有机化学, 2023, 43(4): 1365-1385.
[14]	赵金晓, 魏彤辉, 柯森, 李毅. 可见光催化合成二氟烷基取代的多环吲哚化合物[J]. 有机化学, 2023, 43(3): 1102-1114.
[15]	杜昌远, 唐裕才, 段京林, 杨碧玉, 何宇鹏, 周谦, 刘学文. 可见光促进有机染料催化2-芳基吲哚自由基烷氧羰基化反应研究[J]. 有机化学, 2023, 43(12): 4268-4276.